Updated on 2026/05/09

写真a

 
SEIO KOHJI
 
Organization
School of Life Science and Technology Professor
Title
Professor
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News & Topics

Degree

  • 理学博士 ( 東京工業大学 )

Research Interests

  • ヌクレオチド化学

  • 核酸医薬

  • アンチセンス核酸

  • 有機合成

  • 核酸化学

Research Areas

  • Life Science / Bioorganic chemistry  / 核酸化学 有機合成

  • Life Science / Pharmaceutical chemistry and drug development sciences  / 核酸医薬 ヌクレオチド

Education

  • 東京工業大学大学院   生命理工学研究科   バイオサイエンス専攻

    - 1996

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    Country: Japan

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  • Tokyo Institute of Technology   Graduate School of Bioscience and Biotechnology   Department of Biosicence

    - 1996

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  • Tokyo Institute of Technology   School of Science

    - 1991

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    Country: Japan

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Professional Memberships

Papers

  • Backbone extension by methylene insertion as a strategy to restore duplex stability of sulfonamide-linked oligodeoxynucleotides while preserving RNase H activity

    Kohji Seio, Hiroki Mikagi, Haruka Tanabe, Shigetoshi Tachibana, Yoshiaki Masaki, Eitaro Murakami

    ORGANIC & BIOMOLECULAR CHEMISTRY   2026.4

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    DOI: 10.1039/d6ob00490c

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  • Enzyme-Responsive Cyclic Gapmer Antisense Oligonucleotides via Thymidine C5-C5 Cross-Linking within the Gap Region Using a Galactosylated Branched Self-Immolative Linker

    Kento Miyaji, Narumi Habu, Kohji Seio

    BIOCONJUGATE CHEMISTRY   37 ( 4 )   798 - 806   2026.4

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.bioconjchem.6c00065

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  • Topological Switch-OFF and β-Galactosidase-Triggered Switch-ON of Cyclic Antisense Oligonucleotides via CuAAC for Controlled RNA Cleavage

    Kento Miyaji, Keita Takeuchi, Kohji Seio

    BIOCONJUGATE CHEMISTRY   36 ( 8 )   1820 - 1837   2025.8

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.bioconjchem.5c00295

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  • Synthesis of Prodrug-Type Oligonucleotides Modified With a Galactosylated Self-Immolative Linker Cleavable by β-Galactosidase

    Kento Miyaji, Yoshiaki Masaki, Kohji Seio

    CURRENT PROTOCOLS   5 ( 4 )   2025.4

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/cpz1.70128

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  • Synthesis of LNA gapmers that replace a phosphorothioate linkage with a sulfonamide in the gap region, and their ability to form duplexes with complementary RNA targets

    Kohji Seio, Rie Ohnishi, Shigetoshi Tachibana, Hiroki Mikagi, Yoshiaki Masaki

    ORGANIC & BIOMOLECULAR CHEMISTRY   23 ( 2 )   400 - 409   2025.1

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    DOI: 10.1039/d4ob01350f

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  • Hic-5 antisense oligonucleotide inhibits advanced hepatic fibrosis and steatosis in vivo

    Masahito Noguchi, Aya Miyauchi, Yoshiaki Masaki, Masashi Sakaki, Xiao-Feng Lei, Momoko Kobayashi-Tanabe, Akira Miyazaki, Takeshi Aoki, Hitoshi Yoshida, Kohji Seio, Joo-ri Kim-Kaneyama

    JHEP REPORTS   6 ( 11 )   2024.11

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.jhepr.2024.101195

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  • Inhibitory Effects on RNA Binding and RNase H Induction Activity of Prodrug-Type Oligodeoxynucleotides Modified with a Galactosylated Self-Immolative Linker Cleavable by β-Galactosidase

    Kento Miyaji, Yoshiaki Masaki, Kohji Seio

    BIOCONJUGATE CHEMISTRY   35 ( 10 )   1587 - 1607   2024.10

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    DOI: 10.1021/acs.bioconjchem.4c00376

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  • Synthesis and Conformational Analyses of Cyclonucleoside Having 13-Membered Ring Bridging Nucleobase and 5′-Position via a Linker Containing Sulfonamide

    Takayuki Kanagawa, Shigetoshi Tachibana, Yoshiaki Masaki, Kohji Seio

    ORGANIC LETTERS   25 ( 43 )   7868 - 7872   2023.10

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.orglett.3c03094

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  • Alteration of target cleavage patterns and off-target reduction of antisense oligonucleotides incorporating 2-N-carbamoyl- or (2-pyridyl)guanine International journal

    Takayuki Kanagawa, Aya Koyoma, Yoshiaki Masaki, Kohji Seio

    ORGANIC & BIOMOLECULAR CHEMISTRY   21 ( 25 )   5214 - 5224   2023.6

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    DOI: 10.1039/d3ob00574g

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  • Insertion of a methylene group into the backbone of an antisense oligonucleotide reveals the importance of deoxyribose recognition by RNase H

    Yoshiaki Masaki, Ayano Tabira, Shihori Hattori, Shunsuke Wakatsuki, Kohji Seio

    ORGANIC & BIOMOLECULAR CHEMISTRY   20 ( 45 )   8917 - 8924   2022.11

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/d2ob01667b

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  • Synthesis of 2′-O-[3-(N-methylsulfamoyl)propan-1-yl]ribothymidine as a potentially applicable 2′-modified nucleoside for antisense oligonucleotides

    Takahito Tomori, Koya Uekusa, Aya Koyama, Takayuki Kanagawa, Yoshiaki Masaki, Kohji Seio

    BIOORGANIC & MEDICINAL CHEMISTRY   73   2022.11

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.bmc.2022.117002

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  • Quantification of synthetic errors during chemical synthesis of DNA and its suppression by non-canonical nucleosides

    Yoshiaki Masaki, Yukiko Onishi, Kohji Seio

    SCIENTIFIC REPORTS   12 ( 1 )   2022.7

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/s41598-022-16222-2

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  • Selective and stable base pairing by alkynylated nucleosides featuring a spatially-separated recognition interface

    Hidenori Okamura, Giang Hoang Trinh, Zhuoxin Dong, Yoshiaki Masaki, Kohji Seio, Fumi Nagatsugi

    NUCLEIC ACIDS RESEARCH   50 ( 6 )   3042 - 3055   2022.4

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1093/nar/gkac140

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  • Oligodeoxynucleotides Modified with 2′-O-(Cysteinylaminobutyl)carbamoylethylribothymidine Residues for Native Chemical Ligation with Peptide at Internal Positions

    Yoshiaki Masaki, Atsuya Maruyama, Keita Yoshida, Takahito Tomori, Tomohiro Kishimura, Kohji Seio

    BIOCONJUGATE CHEMISTRY   33 ( 2 )   272 - 278   2022.2

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.bioconjchem.1c00575

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  • Synthesis of 2′-O-alkylcarbamoylethyl-modified oligonucleotides with enhanced nuclease resistance that form isostable duplexes with complementary RNA

    Tomohiro Kishimura, Takahito Tomori, Yoshiaki Masaki, Kohji Seio

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   35   2021.3

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    DOI: 10.1016/j.bmcl.2021.127779

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  • Novel EGFP reporter cell and mouse models for sensitive imaging and quantification of exon skipping

    Yuko Hara, Yoshitaka Mizobe, Yukiko U. Inoue, Yasumasa Hashimoto, Norio Motohashi, Yoshiaki Masaki, Kohji Seio, Shin'ichi Takeda, Tetsuya Nagata, Matthew J. A. Wood, Takayoshi Inoue, Yoshitsugu Aoki

    SCIENTIFIC REPORTS   10 ( 1 )   2020.6

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/s41598-020-67077-4

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  • Synthesis of Deoxypseudouridine 5′-Triphosphate Bearing the Photoremovable Protecting Group at the N1 Position Capable of Enzymatic Incorporation to DNA

    Leo Takeshita, Yuji Yamada, Yoshiaki Masaki, Kohji Seio

    JOURNAL OF ORGANIC CHEMISTRY   85 ( 4 )   1861 - 1870   2020.2

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.9b02194

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  • Transcription of DNA duplex containing deoxypseudouridine and deoxypseudoisocytidine, and inhibition of transcription by triplex forming oligonucleotide that recognizes the modified duplex. International journal

    Kohji Seio, Kei Yamaguchi, Ayano Yamazaki, Takashi Kanamori, Yoshiaki Masaki

    Nucleosides, nucleotides & nucleic acids   39 ( 6 )   892 - 904   2020

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    DOI: 10.1080/15257770.2020.1714652

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  • Crystal structure of a DNA duplex cross-linked by 6-thioguanine-6-thioguanine disulfides: reversible formation and cleavage catalyzed by Cu(ii) ions and glutathione

    Akira Ono, Takahiro Atsugi, Misato Goto, Hisao Saneyoshi, Takahito Tomori, Kohji Seio, Takenori Dairaku, Jiro Kondo

    RSC ADVANCES   9 ( 40 )   22859 - 22862   2019.8

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    DOI: 10.1039/c9ra03515j

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  • A theoretical study on the elimination reaction of acrylonitrile from 2 '-O-cyanoethylated nucleosides by Bu4NF

    Kaori Ando, Hisao Saneyoshi, Kohji Seio, Mitsuo Sekine

    TETRAHEDRON   75 ( 1 )   1 - 9   2019.1

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tet.2018.11.042

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  • DNA triplex-based fluorescence turn-on sensors for adenosine using a fluorescent molecular rotor 5-(3-methylbenzofuran-2-yl) deoxyuridine

    Takashi Kanamori, Yoshiaki Masaki, Yuki Oda, Hiroki Ohzeki, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    Organic and Biomolecular Chemistry   17 ( 8 )   2077 - 2080   2019

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry  

    DOI: 10.1039/C8OB02747A

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  • Modification of oligonucleotides with weak basic residues: Via the 2′-O-carbamoylethyl linker for improving nuclease resistance without loss of duplex stability and antisense activity

    Yoshiaki Masaki, Keishi Yamamoto, Keita Yoshida, Atsuya Maruyama, Takahito Tomori, Yusuke Iriyama, Hiroyuki Nakajima, Tatsuro Kanaki, Kohji Seio

    Organic and Biomolecular Chemistry   17 ( 19 )   4835 - 4842   2019

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    DOI: 10.1039/c9ob00668k

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  • Effects of 2'-O-modifications on RNA duplex stability

    Yoshiaki Masaki, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Synthesis of Therapeutic Oligonucleotides   187 - 199   2018.12

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    Language:English   Publishing type:Part of collection (book)   Publisher:Springer Singapore  

    DOI: 10.1007/978-981-13-1912-9_11

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  • Nucleosides and oligonucleotides incorporating 2-thiothymine or 2-thiouracil derivatives as modified nucleobases

    Kohji Seio, Mitsuo Sekine

    Synthesis of Therapeutic Oligonucleotides   115 - 130   2018.12

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    Language:English   Publishing type:Part of collection (book)   Publisher:Springer Singapore  

    DOI: 10.1007/978-981-13-1912-9_7

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  • Non-protected synthesis of oligonucleotides

    Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Synthesis of Therapeutic Oligonucleotides   3 - 16   2018.12

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    Language:English   Publishing type:Part of collection (book)   Publisher:Springer Singapore  

    DOI: 10.1007/978-981-13-1912-9_1

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  • Synthesis of and triplex formation in oligonucleotides containing 2’-deoxy-6-thioxanthosine Reviewed

    Takeshi Inde, Shuhei Nishizawa, Yuusaku Hattori, Takashi Kanamori, Hideya Yuasa, Kohji Seio, Mitsuo Sekine, Akihiro Ohkubo

    Bioorganic and Medicinal Chemistry   2018.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Elsevier Ltd  

    DOI: 10.1016/j.bmc.2018.06.004

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  • Solvent- and environment-dependent fluorescence of modified nucleobases

    Kohji Seio, Takashi Kanamori, Yoshiaki Masaki

    Tetrahedron Letters   59 ( 21 )   1977 - 1985   2018.5

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    Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.tetlet.2018.04.003

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  • Synthesis of photocaged6-O-(2-nitrobenzyl) guanosine and 4-O-(2-nitrobenzyl)uridine triphosphates for photocontrol of the RNA transcription reaction Reviewed

    Kentaro Ohno, Daiki Sugiyama, Leo Takeshita, Takashi Kanamori, Yoshiaki Masaki, Mitsuo Sekine, Kohji Seio

    BIOORGANIC & MEDICINAL CHEMISTRY   25 ( 21 )   6007 - 6015   2017.11

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.bmc.2017.09.032

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  • Synthesis of oligonucleotides containing 2-N-heteroarylguanine residues and their effect on duplex/triplex stability Reviewed

    Takeshi Inde, Yoshiaki Masaki, Atsuya Maruyama, Yu Ito, Naoaki Makio, Yuya Miyatake, Takahito Tomori, Mitsuo Sekine, Kohji Seio

    ORGANIC & BIOMOLECULAR CHEMISTRY   15 ( 39 )   8371 - 8383   2017.10

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    DOI: 10.1039/c7ob01875d

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  • Deformability calculation for estimation of the relative stability of chemically modified RNA duplexes Reviewed

    Yoshiaki Masaki, Mitsuo Sekine, Kohji Seio

    Current Protocols in Nucleic Acid Chemistry   2017   7.27.1 - 7.27.10   2017.3

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    DOI: 10.1002/cpnc.25

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  • Fluorescence enhancement of oligodeoxynucleotides modified with green fluorescent protein chromophore mimics upon triplex formation Reviewed

    Takashi Kanamori, Akihiro Takamura, Nobuhiro Tago, Yoshiaki Masaki, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    ORGANIC & BIOMOLECULAR CHEMISTRY   15 ( 5 )   1190 - 1197   2017.2

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c6ob01278g

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  • Photo-controlled binding of MutS to photo-caged DNA duplexes incorporating 4-O-(2-nitrobenzyl) or 4-O-[2-(2-nitrophenyl) propyl]thymidine Reviewed

    Kohji Seio, Yurie Ohno, Kentaro Ohno, Leo Takeshita, Takashi Kanamori, Yoshiaki Masaki, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   26 ( 19 )   4861 - 4863   2016.10

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    DOI: 10.1016/j.bmcl.2016.07.075

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  • Synthesis and Fluorescence Properties of Nucleosides with Pyrimidopyrimidine-Type Base Moieties Reviewed

    Kohji Seio, Takashi Kanamori, Akihiro Ohkubo, Mitsuo Sekine

    Fluorescent Analogs of Biomolecular Building Blocks: Design and Applications   208 - 223   2016.4

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    Language:English   Publishing type:Part of collection (book)   Publisher:wiley  

    DOI: 10.1002/9781119179320.ch9

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  • Synthesis of 5-[3-(2-aminopyrimidin-4-yl)aminopropyn-1-yl]uracil derivative that recognizes Ade-Thy base pairs in double-stranded DNA Reviewed

    Yu Ito, Yoshiaki Masaki, Takashi Kanamori, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   26 ( 1 )   194 - 196   2016.1

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    DOI: 10.1016/j.bmcl.2015.11.003

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  • Enzymatic synthesis and reverse transcription of RNAs incorporating 2 '-O-carbamoyl uridine triphosphate Reviewed

    Yoshiaki Masaki, Hyugo Ito, Yuki Oda, Kazufumi Yamazaki, Nobuhiro Tago, Kentaro Ohno, Nozomi Ishii, Hirosuke Tsunoda, Takashi Kanamori, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    CHEMICAL COMMUNICATIONS   52 ( 87 )   12889 - 12892   2016

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c6cc05796a

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  • Effective strategy for conformer-selective detection of short-lived excited state species: application to the IR spectroscopy of the N1H keto tautomer of guanine Reviewed

    Hiroya Asami, Munefumi Tokugawa, Yoshiaki Masaki, Shun-ichi Ishiuchi, Eric Gloaguen, Kohji Seio, Hiroyuki Saigusa, Masaaki Fujii, Mitsuo Sekine, Michel Mons

    Journal of Physical Chemistry A   2016

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    DOI: 10.1021/acs.jpca.6b01194

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  • 7-(Benzofuran-2-yl)-7-deazadeoxyguanosine as a fluorescence turn-ON probe for single-strand DNA binding protein Reviewed

    Munefumi Tokugawa, Yoshiaki Masaki, Jan Christian Canggadibrata, Kazuhei Kaneko, Takashi Shiozawa, Takashi Kanamori, Morten Grotli, L. Marcus Wilhelmsson, Mitsuo Sekine, Kohji Seio

    CHEMICAL COMMUNICATIONS   52 ( 19 )   3809 - 3812   2016

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    DOI: 10.1039/c5cc09700b

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  • A New Microfluidic Phase-Transfer Reaction Using HPLC Guard Columns as the Reactor for the N-3-Protection of Uridine Derivatives Reviewed

    Nobuhiro Tago, Yoshiaki Masaki, Hiroshi Nagasawa, Takashi Kanamori, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    SYNLETT   26 ( 18 )   2578 - 2582   2015.11

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0035-1560264

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  • Design, Synthesis, and Properties of Phosphoramidate 2 ',5 '-Linked Branched RNA: Toward the Rational Design of Inhibitors of the RNA Lariat Debranching Enzyme Reviewed

    Nobuhiro Tago, Adam Katolik, Nathaniel E. Clark, Eric J. Montemayor, Kohji Seio, Mitsuo Sekine, P. John Hart, Masad J. Damha

    JOURNAL OF ORGANIC CHEMISTRY   80 ( 20 )   10108 - 10118   2015.10

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    DOI: 10.1021/acs.joc.5b01719

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  • Synthesis and triplex-forming properties of oligonucleotides capable of recognizing corresponding DNA duplexes containing four base pairs Reviewed

    Akihiro Ohkubo, Kenji Yamada, Yu Ito, Kiichi Yoshimura, Koichiro Miyauchi, Takashi Kanamori, Yoshiaki Masaki, Kohji Seio, Hideya Yuasa, Mitsuo Sekine

    NUCLEIC ACIDS RESEARCH   43 ( 12 )   5675 - 5686   2015.7

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    DOI: 10.1093/nar/gkv496

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  • Synthesis of Peptide Nucleic Acids Containing Pyridazine Derivatives As Cytosine and Thymine Analogs, and Their Duplexes with Complementary Oligodeoxynucleotides Reviewed

    Takahito Tomori, Yuya Miyatake, Yuta Sato, Takashi Kanamori, Yoshiaki Masaki, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    ORGANIC LETTERS   17 ( 6 )   1609 - 1612   2015.3

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    DOI: 10.1021/acs.orglett.5b00522

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  • Controlling the Fluorescence of Benzofuran-Modified Uracil Residues in Oligonucleotides by Triple-Helix Formation Reviewed

    Takashi Kanamori, Hiroki Ohzeki, Yoshiaki Masaki, Akihiro Ohkubo, Mari Takahashi, Kengo Tsuda, Takuhiro Ito, Mikako Shirouzu, Kanako Kuwasako, Yutaka Muto, Mitsuo Sekine, Kohji Seio

    CHEMBIOCHEM   16 ( 1 )   167 - 176   2015.1

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/cbic.201402346

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  • Synthesis of Responsive Fluorescent Nucleobases 7-(Benzofuran-2-yl)-7-deazahypoxanthine and 7-(Benzofuran-2-yl)-7-deazaguanine Using Cross-coupling Reaction Reviewed

    Munefumi Tokugawa, Kazuhei Kaneko, Masanori Saito, Takashi Kanamori, Yoshiaki Masaki, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    CHEMISTRY LETTERS   44 ( 1 )   64 - 66   2015.1

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    DOI: 10.1246/cl.140879

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  • Enhancement of exon skipping in mdx52 mice by 2′-O-methyl-2-thioribothymidine incorporation into phosphorothioate oligonucleotides

    Yoshiaki Masaki, Takeshi Inde, Tetsuya Nagata, Jun Tanihata, Takashi Kanamori, Kohji Seio, Shin'ichi Takeda, Mitsuo Sekine

    MedChemComm   6 ( 4 )   630 - 633   2015

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    Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    <p>Incorporation of 2′-O-methyl-2-thioribothymidine (s2Tm) into antisense oligoribonucleotides significantly enhanced the exon skipping activity in Duchenne muscular dystrophy model mice.</p>

    DOI: 10.1039/c4md00468j

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  • Synthesis and exon-skipping activity of chemically modified RNAs

    Yoshiaki Masaki, Takeshi Yamada, Hisao Saneyoshi, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Chemical Biology of Nucleic Acids: Fundamentals and Clinical Applications   497 - 510   2014.1

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    Language:English   Publishing type:Part of collection (book)   Publisher:Springer Berlin Heidelberg  

    DOI: 10.1007/978-3-642-54452-1_27

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  • Synthesis and properties of base or sugar modified RNA derivatives Invited

    Mitsuo Sekine, Yoshiaki Masaki, Takeshi Yamada, Youdai Ishii, Keishi Yamamoto, Natsuki Okaniwa, Takeshi Kanamori, Hisashi Saneyoshi, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio

    Collection of Czechoslovak Chemical Communications   14   167 - 170   2014

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    Language:English   Publishing type:Research paper (international conference proceedings)   Publisher:Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic  

    DOI: 10.1135/css201414167

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  • Synthesis of branched DNA using oxidatively cleavable tritylsulfenyl as a hydroxy protecting group Reviewed

    Kohji Seio, Takashi Kanamori, Mitsuo Sekine

    Current Protocols in Nucleic Acid Chemistry   2014   2.18.1 - 2.18.19   2014

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Blackwell Publishing Inc.  

    DOI: 10.1002/0471142700.nc0218s58

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  • Properties of 5- and/or 2-modified 2 '-O-cyanoethyl uridine residue: 2 '-O-cyanoethyl-5-propynyl-2-thiouridine as an efficient duplex stabilizing component Reviewed

    Yoshiaki Masaki, Ryuta Miyasaka, Kunihiro Hirai, Takashi Kanamori, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    ORGANIC & BIOMOLECULAR CHEMISTRY   12 ( 7 )   1157 - 1162   2014

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c3ob41983e

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  • A new modified cytosine base capable of base pairing with guanine using four hydrogen bonds Reviewed

    Ken Yamada, Yoshiaki Masaki, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    ORGANIC & BIOMOLECULAR CHEMISTRY   12 ( 14 )   2255 - 2262   2014

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c3ob42420k

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  • Synthesis and properties of oligonucleotides modified with 2 '-O-(2-carboxyethyl)nucleotides and their carbamoyl derivatives Reviewed

    Takeshi Yamada, Yoshiaki Masaki, Natsuki Okaniwa, Takashi Kanamori, Akihiro Ohkubo, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    ORGANIC & BIOMOLECULAR CHEMISTRY   12 ( 33 )   6457 - 6464   2014

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    DOI: 10.1039/c4ob01260g

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  • Assembly of pyrene-modified DNA/RNA duplexes incorporating a G-rich single strand region Reviewed

    Kohji Seio, Munefumi Tokugawa, Hirosuke Tsunoda, Akihiro Ohkubo, Fumio Arisaka, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   23 ( 24 )   6822 - 6824   2013.12

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  • Modified oligodeoxynucleotide primers for reverse-transcription of target RNAs that can discriminate among length variants at the 3 '-terminus Reviewed

    Yoshihiro Iijima, Shun Kojima, Erika Kodama, Sayako Kurohagi, Takashi Kanamori, Yoshiaki Masaki, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    ORGANIC & BIOMOLECULAR CHEMISTRY   11 ( 47 )   8276 - 8282   2013.12

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    DOI: 10.1039/c3ob41901k

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  • Chemical Synthesis of U1 snRNA Derivatives Reviewed

    Akihiro Ohkubo, Yasushi Kondo, Makoto Suzuki, Haruki Kobayashi, Takashi Kanamori, Yoshiaki Masaki, Kohji Seio, Kiyoshi Nagai, Mitsuo Sekine

    ORGANIC LETTERS   15 ( 17 )   4386 - 4389   2013.9

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  • Fluorescent properties of oligonucleotides doubly modified with an indole-fused cytosine analog and 2-aminopurine. International journal

    Kohji Seio, Takashi Kanamori, Munefumi Tokugawa, Hiroki Ohzeki, Yoshiaki Masaki, Hirosuke Tsunoda, Akihiro Ohkubo, Mitsuo Sekine

    Bioorganic & medicinal chemistry   21 ( 11 )   3197 - 201   2013.6

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    Single- and double-stranded oligodeoxynucleotides (ODNs) incorporating both 2-aminopurine (2AP) and an indole-fused cytosine analog (PPI) were prepared and studied for their fluorescence properties. PPI and 2AP can be excited simultaneously by irradiation at 300 nm, with emission observed at 500 nm for PPI and 370 nm for 2AP. We demonstrated the utility of these properties in the dual fluorescence labeling of ODNs giving well-separated emission peaks. In addition, both of the fluorescence signals of a doubly modified ODN changed independently, reflecting the local duplex formation at the regions containing 2AP or PPI. Potential applications of this strategy for the dual fluorescence labeling of oligonucleotides with 2AP and PPI include monitoring local structure alterations of functional nucleic acids and the multiplex detection of biologically important nucleic acids.

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  • Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups

    Kenji Yamada, Yusaku Hattori, Takeshi Inde, Takashi Kanamori, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Bioorganic and Medicinal Chemistry Letters   23 ( 3 )   776 - 778   2013.2

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    DOI: 10.1016/j.bmcl.2012.11.079

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  • DNA-maleimide: An improved maleimide compound for electrophoresis-based titration of reactive thiols in a specific protein Reviewed

    Hara Satoshi, Nojima Tatsuya, Seio Kohji, Yoshida Masasuke, Hisabori Toru

    Biochimica Et Biophysica Acta-General Subjects   1830 ( 4 )   3077 - 3081   2013

  • Synthesis and properties of cationic 2 '-O-[N-(4-aminobutyl)carbamoyl] modified oligonucleotides Reviewed

    Kohji Seio, Munefumi Tokugawa, Takashi Kanamori, Hirosuke Tsunoda, Akihiro Ohkubo, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   22 ( 7 )   2470 - 2473   2012.4

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    DOI: 10.1016/j.bmcl.2012.02.012

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  • Development of an efficient method for phosphorodiamidate bond formation by using inorganic salts Reviewed

    Taro Harakawa, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   22 ( 3 )   1445 - 1447   2012.2

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    DOI: 10.1016/j.bmcl.2011.12.021

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  • Synthesis of 5 '-Terminal Capped Oligonucleotides Using O-N Phosphoryl Migration of Phosphoramidite Derivatives Reviewed

    Akihiro Ohkubo, Nobuhiro Tago, Akira Yokouchi, Yudai Nishino, Ken Yamada, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    ORGANIC LETTERS   14 ( 1 )   10 - 13   2012.1

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    DOI: 10.1021/ol2026075

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  • Formation of new base pairs between inosine and 5-methyl-2-thiocytidine derivatives Reviewed

    Akihiro Ohkubo, Yudai Nishino, Yu Ito, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    ORGANIC & BIOMOLECULAR CHEMISTRY   10 ( 10 )   2008 - 2010   2012

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    DOI: 10.1039/c2ob06641f

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  • DNA duplexes and triplex-forming oligodeoxynucleotides incorporating modified nucleosides forming stable and selective triplexes Reviewed

    Takashi Kanamori, Yoshiaki Masaki, Masahiro Mizuta, Hirosuke Tsunoda, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    ORGANIC & BIOMOLECULAR CHEMISTRY   10 ( 5 )   1007 - 1013   2012

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    DOI: 10.1039/c1ob06411h

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  • Prediction of the stability of modified RNA duplexes based on deformability analysis: oligoribonucleotide derivatives modified with 2 '-O-cyanoethyl-5-propynyl-2-thiouridine as a promising component Reviewed

    Yoshiaki Masaki, Ryuta Miyasaka, Kunihiro Hirai, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    CHEMICAL COMMUNICATIONS   48 ( 58 )   7313 - 7315   2012

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    DOI: 10.1039/c2cc33409g

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  • Short-RNA selective binding of oligonucleotides modified using adenosine and guanosine derivatives that possess cyclohexyl phosphates as substituents Reviewed

    Kohji Seio, Sayako Kurohagi, Erika Kodama, Yoshiaki Masaki, Hirosuke Tsunoda, Akihiro Ohkubo, Mitsuo Sekine

    ORGANIC & BIOMOLECULAR CHEMISTRY   10 ( 5 )   994 - 1006   2012

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    DOI: 10.1039/c1ob06580g

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  • Synthesis of 2 &apos;-O-[2-(N-Methylcarbamoyl)ethyl]ribonucleosides Using Oxa-Michael Reaction and Chemical and Biological Properties of Oligonucleotide Derivatives Incorporating These Modified Ribonucleosides Reviewed

    Takeshi Yamada, Natsuki Okaniwa, Hisao Saneyoshi, Akihiro Ohkubo, Kohji Seio, Tetsuya Nagata, Yoshitsugu Aoki, Shin&apos;ichi Takeda, Mitsuo Sekine

    JOURNAL OF ORGANIC CHEMISTRY   76 ( 9 )   3042 - 3053   2011.5

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    DOI: 10.1021/jo101963z

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  • Biochemical behavior of N-oxidized cytosine and adenine bases in DNA polymerase-mediated primer extension reactions Reviewed

    Hirosuke Tsunoda, Tomomi Kudo, Yoshiaki Masaki, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    NUCLEIC ACIDS RESEARCH   39 ( 7 )   2995 - 3004   2011.4

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    DOI: 10.1093/nar/gkq914

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  • Synthesis and triplex-forming properties of oligonucleotides containing thio-substituted C-nucleoside 4-thiopseudoisocytidine Reviewed

    Shi-Qi Cao, Itaru Okamoto, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    TETRAHEDRON LETTERS   52 ( 3 )   407 - 410   2011.1

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    DOI: 10.1016/j.tetlet.2010.11.065

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  • Stable triplex formation using the strong stacking effect of consecutive thionucleoside moieties Reviewed

    Akihiro Ohkubo, Yudai Nishino, Akira Yokouchi, Yu Ito, Yasuhiro Noma, Yuuki Kakishima, Yoshiaki Masaki, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    CHEMICAL COMMUNICATIONS   47 ( 46 )   12556 - 12558   2011

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    DOI: 10.1039/c1cc14339e

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  • Synthesis and hybridization properties of 2 '-O-methylated oligoribonucleotides incorporating 2 '-O-naphthyluridines Reviewed

    Mitsuo Sekine, Yusuke Oeda, Yoshihiro Iijima, Haruhiko Taguchi, Akihiro Ohkubo, Kohji Seio

    ORGANIC & BIOMOLECULAR CHEMISTRY   9 ( 1 )   210 - 218   2011

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    DOI: 10.1039/c0ob00248h

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  • Synthesis and biological properties of 2'-O-modified oligoribonucleotide derivatives Invited

    Takeshi Yamada, Natsuki Okaniwa, Yoshiaki Masaki, Yasuhiro Okuno, Ryuta Miyasaka, Hiroyuki Tsunoda, Akihiro Ohkubo, Kohji Seio, Tetsuya Nagata, Yoshitsugu Aoki, Shin'ichi Takeda, Mitsuo Sekine

    Collection of Czechoslovak Chemical Communications   12   240 - 243   2011

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  • Synthesis of Oligodeoxynucleotides Using Fully Protected Deoxynucleoside 3 &apos;-Phosphoramidite Building Blocks and Base Recognition of Oligodeoxynucleotides Incorporating N-3-Cyano-Ethylthymine Reviewed

    Hirosuke Tsunoda, Tomomi Kudo, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    MOLECULES   15 ( 11 )   7509 - 7531   2010.11

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    DOI: 10.3390/molecules15117509

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  • Synthesis and biochemical properties of oligodeoxynucleotides acylated by the chemically stable 2-(trimethylsilyl)benzoyl (TMSBz) group at the 5 &apos; or 3 &apos; terminus Reviewed

    Ken Yamada, Haruhiko Taguchi, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    TETRAHEDRON LETTERS   51 ( 39 )   5173 - 5176   2010.9

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    DOI: 10.1016/j.tetlet.2010.07.121

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  • Synthesis and Hybridization Properties of Oligonucleotides Incorporating Bi- and Tricyclic Cytosine Derivatives Reviewed

    Akihiro Ohkubo, Toshiyuki Sakaue, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    CHEMISTRY LETTERS   39 ( 7 )   726 - 727   2010.7

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    DOI: 10.1246/cl.2010.726

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  • Oligonucleotide Synthesis Involving Deprotection of Amidine-Type Protecting Groups for Nucleobases under Acidic Conditions Reviewed

    Akihiro Ohkubo, Yasukazu Kuwayama, Yudai Nishino, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    ORGANIC LETTERS   12 ( 11 )   2496 - 2499   2010.6

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    DOI: 10.1021/ol100676j

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  • Linear Relationship between Deformability and Thermal Stability of 2 &apos;-O-Modified RNA Hetero Duplexes Reviewed

    Yoshiaki Masaki, Ryuta Miyasaka, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    JOURNAL OF PHYSICAL CHEMISTRY B   114 ( 7 )   2517 - 2524   2010.2

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  • Synthesis of 6-N-(benzothiazol-2-yl)deoxyadenosine and its exciton-coupled circular dichroism Reviewed

    Yoshiaki Masaki, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY   18 ( 2 )   567 - 572   2010.1

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    DOI: 10.1016/j.bmc.2009.12.009

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  • Synthesis of oligodeoxynucleotides using the oxidatively cleavable 4-methoxytritylthio (MMTrS) group for protection of the 5 &apos;-hydroxyl group Reviewed

    Kohji Seio, Miyuki Shiraishi, Eri Utagawa, Akihiro Ohkubo, Mitsuo Sekine

    NEW JOURNAL OF CHEMISTRY   34 ( 5 )   984 - 992   2010

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    DOI: 10.1039/b9nj00678h

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  • Synthesis and hybridization of 2 &apos;-O-methyl-RNAs incorporating 2 &apos;-O-carbamoyluridine and unique participation of the carbamoyl group in U-G base pair Reviewed

    Kohji Seio, Ryuya Tawarada, Takeshi Sasami, Masashi Serizawa, Misako Ise, Akihiro Ohkubo, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY   17 ( 20 )   7275 - 7280   2009.10

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    DOI: 10.1016/j.bmc.2009.08.053

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  • Synthesis and properties of nucleoside derivatives acylated by chemically stable 2-(trimethylsilyl)benzoyl group Reviewed

    Ken Yamada, Haruhiko Taguchi, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY   17 ( 16 )   5928 - 5932   2009.8

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    DOI: 10.1016/j.bmc.2009.07.003

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  • Fluorescence Properties of Pyrimidopyrimidoindole Nucleoside dC(PPI) Incorporated into Oligodeoxynucleotides Reviewed

    Masahiro Mizuta, Kohji Seio, Akihiro Ohkubo, Mitsuo Sekine

    JOURNAL OF PHYSICAL CHEMISTRY B   113 ( 28 )   9562 - 9569   2009.7

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    DOI: 10.1021/jp807562c

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  • Efficient solid-phase synthesis of oligodeoxynucleotides having a 5 &apos;-terminal 2,2,7-trimethylguanosine pyrophosphate linkage Reviewed

    Akihiro Ohkubo, Kenji Sasaki, Yasuhiro Noma, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY   17 ( 13 )   4819 - 4824   2009.7

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    DOI: 10.1016/j.bmc.2009.04.073

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  • Introduction of 3 &apos;-Terminal Nucleosides Having a Silyl-Type Linker into Polymer Supports without Base Protection Reviewed

    Akihiro Ohkubo, Yasuhiro Noma, Katsufumi Aoki, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    JOURNAL OF ORGANIC CHEMISTRY   74 ( 7 )   2817 - 2823   2009.4

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    DOI: 10.1021/jo9000965

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  • Computational evaluation of the stability of 2 &apos;-O-methyl-RNA/RNA duplexes incorporating 3-deazaguanine derivatives by ab initio calculations and a molecular dynamics simulation Reviewed

    Takeshi Sasami, Ryuya Tawarada, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM   899 ( 1-3 )   54 - 60   2009.4

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    DOI: 10.1016/j.theochem.2008.12.012

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  • Synthesis of oligodeoxynucleotides incorporating 2-N-carbamoylguanine and evaluation of the hybridization properties Reviewed

    Takeshi Sasami, Yoko Odawara, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    BIOORGANIC & MEDICINAL CHEMISTRY   17 ( 3 )   1398 - 1403   2009.2

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  • Synthesis of 4-Thiopseudoisocytidine and 4-Thiopseudouridine as Components of Triplex-forming Oligonucleotides Reviewed

    Itaru Okamoto, Shiqi Cao, Hiroto Tanaka, Kohji Seio, Mitsuo Sekine

    CHEMISTRY LETTERS   38 ( 2 )   174 - 175   2009.2

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    DOI: 10.1246/cl.2009.174

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  • Synthesis and Triplex Formation of Oligonucleotides Containing 8-Thioxodeoxyadenosine Reviewed

    Ken-ichi Miyata, Ryuji Tamamushi, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    ORGANIC LETTERS   11 ( 3 )   605 - 608   2009.2

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    DOI: 10.1021/ol802622s

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  • Synthesis and triplex formation of oligonucleotides containing 8-thioxodeoxyadenosine and 5-methyl-2-thiodeoxycytosine.

    Akihiro Ohkubo, Kenichi Miyata, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    Nucleic acids symposium series (2004)   ( 53 )   21 - 22   2009

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    DOI: 10.1093/nass/nrp011

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  • Evaluation of base recognition abilities of 2'-deoxynucleoside N-oxide derivatives by polymerase reactions.

    Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Nucleic acids symposium series (2004)   ( 53 )   127 - 128   2009

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    DOI: 10.1093/nass/nrp064

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  • Development of new DNA triplex triads by using 5-substituted deoxycytidine.

    Takashi Kanamori, Hirosuke Tsunoda, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    Nucleic acids symposium series (2004)   ( 53 )   163 - 164   2009

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    DOI: 10.1093/nass/nrp082

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  • Mechanistic studies on oxidative condensation of a thymidine 3 &apos;-H-phosphonate derivative with 3 &apos;-O-acetylthymidine Reviewed

    Ryuuya Tawarada, Kohji Seio, Mitsuo Sekine

    ARKIVOC   264 - 273   2009

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  • Synthesis and hybridization properties of oligonucleotides having 4-N-(pyrrol-2-ylcarbonyl)deoxycytidine.

    Ken Yamada, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Nucleic acids symposium series (2004)   ( 53 )   115 - 116   2009

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    DOI: 10.1093/nass/nrp058

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  • Synthesis and properties of terminally modified oligonucleotides capable of short-RNA selective hybridization.

    Kohji Seio, Kazuya Miyazaki, Sayako Kurohagi, Yoshiaki Masaki, Hirosuke Tsunoda, Akihiro Ohkubo, Mitsuo Sekine

    Nucleic acids symposium series (2004)   ( 53 )   13 - 14   2009

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    DOI: 10.1093/nass/nrp007

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  • Synthesis of terminally modified oligonucleotides and their hybridization dependence on the size of the target RNAs Reviewed

    Kohji Seio, Yusuke Takaku, Kazuya Miyazaki, Sayako Kurohagi, Yoshiaki Masaki, Akihiro Ohkubo, Mitsuo Sekine

    ORGANIC & BIOMOLECULAR CHEMISTRY   7 ( 11 )   2440 - 2451   2009

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    DOI: 10.1039/b900301k

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  • New thermolytic carbamoyl groups for the protection of nucleobases Reviewed

    Akihiro Ohkubo, Rintaro Kasuya, Kenichi Miyata, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    ORGANIC & BIOMOLECULAR CHEMISTRY   7 ( 4 )   687 - 694   2009

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    DOI: 10.1039/b816831h

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  • Hybridization-dependent fluorescence of oligodeoxynucleotides incorporating new pyrene-modified adenosine residues Reviewed

    Kohji Seio, Masanhiro Mizuta, Kaori Tasaki, Keigo Tamaki, Akihiro Ohkubo, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY   16 ( 17 )   8287 - 8293   2008.9

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    DOI: 10.1016/j.bmc.2008.05.042

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  • New nucleotide pairs for stable DNA triplexes stabilized by stacking interaction Reviewed

    Masahiro Mizuta, Jun-ichi Banba, Takashi Kanamori, Ryuya Tawarada, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   130 ( 30 )   9622 - +   2008.7

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    DOI: 10.1021/ja800991m

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  • O-selective condensation using P-N bond cleavage in RNA synthesis without base protection Reviewed

    Akihiro Ohkubo, Yasukazu Kuwayama, Tomomi Kudo, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    ORGANIC LETTERS   10 ( 13 )   2793 - 2796   2008.7

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    DOI: 10.1021/ol800911b

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  • Study of the base discrimination ability of DNA and 2 &apos;-O-methylated RNA oligomers containing 2-thiouracil bases towards complementary RNA or DNA strands and their application to single base mismatch detection Reviewed

    Itaru Okamoto, Kohji Seio, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY   16 ( 11 )   6034 - 6041   2008.6

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    DOI: 10.1016/j.bmc.2008.04.053

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  • Efficient synthesis of functionalized oligodeoxyribonucleotides with base-labile groups using a new silyl linker Reviewed

    Akihiro Ohkubo, Rintaro Kasuya, Katsufumi Aoki, Akio Kobori, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY   16 ( 9 )   5345 - 5351   2008.5

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    DOI: 10.1016/j.bmc.2008.02.076

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  • Synthesis and hybridization properties of 2 '-O-(tetrazol-5-yl)ethyl-modified oligonucleotides Reviewed

    Hisao Saneyoshi, Keigo Tamaki, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    TETRAHEDRON   64 ( 19 )   4370 - 4376   2008.5

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    DOI: 10.1016/j.tet.2008.02.075

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  • 'Protected DNA Probes' capable of strong hybridization without removal of base protecting groups Reviewed

    Akihiro Ohkubo, Rintaro Kasuya, Kazushi Sakamoto, Kenichi Miyata, Haruhiko Taguchi, Hiroshi Nagasawa, Toshifumi Tsukahara, Takuma Watanobe, Yoshiyuki Maki, Kohji Seio, Mitsuo Sekine

    NUCLEIC ACIDS RESEARCH   36 ( 6 )   1952 - 1964   2008.4

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    DOI: 10.1093/nar/gkm927

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  • Synthesis and properties of DNA oligomers containing 2 &apos;-deoxynucleoside N-oxide derivatives Reviewed

    Hirosuke Tsunoda, Akihiro Ohkubo, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

    JOURNAL OF ORGANIC CHEMISTRY   73 ( 4 )   1217 - 1224   2008.2

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    DOI: 10.1021/jo7021845

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  • Synthesis and properties of oligonucleotides with iodo-substituted aromatic aglycons: Investigation of possible halogen bonding base pairs Reviewed

    Ryuya Tawarada, Kohji Seio, Mitsuo Sekine

    JOURNAL OF ORGANIC CHEMISTRY   73 ( 2 )   383 - 390   2008.1

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    DOI: 10.1021/jo701634t

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  • Synthesis and properties of oligodeoxynucleotides containing 5-carboxy-2'-deoxycytidines Reviewed

    Masanori Sumino, Akihiro Ohkubo, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   18 ( 1 )   274 - 277   2008.1

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    DOI: 10.1016/j.bmcl.2007.10.081

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  • Protected DNA probes (PDP): A new strategy for gene detection Reviewed

    Akihiro Ohkubo, Itaru Okamoto, Rintaro Kasuya, Kazushi Sakamoto, Takeshi Sasami, Yoko Odawara, Yoshiaki Masaki, Toshiyuki Sakaue, Hiroshi Nagasawa, Toshifumi Tsukahara, Kohji Seio, Mitsuo Sekine

    CHEMISTRY OF NUCLEIC ACID COMPONENTS   10   94 - 102   2008

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  • An effective method for the in situ synthesis of DNA-CPG conjugates using chemical ligation technology as tools for SNP analysis

    Akihiro Ohkubo, Kunihiko Tanaka, Haruhiko Taguchi, Kohji Seio, Hiroshi Nagasawa, Toshifumi Tsukahara, Mitsuo Sekine

    Bioorganic and Medicinal Chemistry Letters   17   5969 - 5973   2007.11

  • Chemical synthesis of RNA via 2 '-O-cyanoethylated intermediates

    Hisao Saneyoshi, Kaori Ando, Kohji Seio, Mitsuo Sekine

    TETRAHEDRON   63 ( 45 )   11195 - 11203   2007.11

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    DOI: 10.1016/j.tet.2007.07.102

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  • Facile synthesis of 2 '-O-cyanoethyluridine by ring-opening reaction of 2,2 '-anhydrouridine with cyanoethyl trimethylsilyl ether in the presence of BF3 center dot Et2O Reviewed

    Hisao Saneyoshi, Itaru Okamoto, Yoshiaki Masaki, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    TETRAHEDRON LETTERS   48 ( 48 )   8554 - 8557   2007.11

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    DOI: 10.1016/j.tetlet.2007.09.105

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  • Synthesis of branched Oligonucleotides with three different sequences using an oxidatively removable tritylthio group Reviewed

    Eri Utagawa, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    JOURNAL OF ORGANIC CHEMISTRY   72 ( 22 )   8259 - 8266   2007.10

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    DOI: 10.1021/jo071173a

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  • Fluorescent pyrimidopyrimidoindole nucleosides: Control of photophysical characterizations by substituent effects Reviewed

    Masahiro Mizuta, Kohji Seio, Kenichi Miyata, Mitsuo Sekine

    JOURNAL OF ORGANIC CHEMISTRY   72 ( 14 )   5046 - 5055   2007.7

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    DOI: 10.1021/jo070206j

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  • A new hydrophobic linker effective for the in situ synthesis of DNA-CPG conjugates as tools for SNP analysis Reviewed

    Akihiro Ohkubo, Haruhiko Taguchi, Kohji Seio, Hiroshi Nagasawa, Toshifumi Tsukahara, Mitsuo Sekine

    TETRAHEDRON LETTERS   48 ( 29 )   5147 - 5150   2007.7

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    DOI: 10.1016/j.tetlet.2007.05.047

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  • Synthesis and hybridization properties of oligodeoxynucleotides incorporating 2-N-carbamoylguanine derivatives as guanine analogs Reviewed

    Takeshi Sasami, Yoko Odawara, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    TETRAHEDRON LETTERS   48 ( 30 )   5325 - 5329   2007.7

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    DOI: 10.1016/j.tetlet.2007.05.038

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  • Chemical properties of 4,5-di(ethoxycarbonyl)-1,3-dioxolan-2-yl (DECDO) as a hydroxyl protecting group of the 2 '-hydroxyl function in ribonucleosides Reviewed

    Boleslaw Karwowski, Kohji Seio, Mitsuo Sekine

    JOURNAL OF HETEROCYCLIC CHEMISTRY   44 ( 2 )   329 - 336   2007.3

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  • Highly selective recognition of cytosine over uracil and adenine by a guanine analogue, 2-N-Acetyl-3-deazaguanine, in 2 '-O-Methyl-RNA/RNA and DNA duplexes

    Kohji Seio, Takeshi Sasami, Akihiro Ohkubo, Kaori Ando, Mitsuo Sekine

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   129 ( 5 )   1026 - 1027   2007.2

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    DOI: 10.1021/ja064612g

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  • A pyrimidopyrimidoindole nucleoside (dC(PPI)): Photophysical properties and thermal stability of the modified DNA duplexes Reviewed

    Masahiro Mizuta, Kohji Seio, Kenichi Miyata, Akihiro Ohkubo, Haruhiko Taguchi, Mitsuo Sekine

    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS   26 ( 10-12 )   1335 - 1338   2007

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    DOI: 10.1080/15257770701533164

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  • Development of an N-unprotected phosphoramidite method for the chemical synthesis of aminoacylated RNAs.

    Akihiro Ohkubo, Yasuhiro Noma, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

    Nucleic acids symposium series (2004)   ( 51 )   1 - 2   2007

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    DOI: 10.1093/nass/nrm001

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  • Recognition of triplex forming oligodeoxynucleotides incorporating abasic sites by 5-arylcytosine residues in duplex DNAs.

    Masahiro Mizuta, Jun-Ichi Banba, Takashi Kanamori, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    Nucleic acids symposium series (2004)   ( 51 )   25 - 26   2007

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    DOI: 10.1093/nass/nrm013

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  • Development of a new method for the synthesis of oligodeoxynucleotides by use of carbamoyl-type protecting groups.

    Akihiro Ohkubo, Rintaro Kasuya, Kenichi Miyata, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

    Nucleic acids symposium series (2004)   ( 51 )   131 - 132   2007

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    DOI: 10.1093/nass/nrm066

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  • Recognition of target chain-length by use of oligonucleotides having bulky substituents at the terminal bases.

    Yusuke Takaku, Masahiro Mizuta, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    Nucleic acids symposium series (2004)   ( 51 )   283 - 284   2007

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    DOI: 10.1093/nass/nrm142

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  • Synthesis and properties of oligodeoxynucleotides incorporating 5-carboxydeoxycytidine.

    Masanori Sumino, Okamoto Itaru, Akihiro Ohkubo, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

    Nucleic acids symposium series (2004)   ( 51 )   165 - 166   2007

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    DOI: 10.1093/nass/nrm083

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  • Short-step chemical synthesis of DNA by use of MMTrS group for protection of 5'-hydroxyl group.

    Miyuki Shiraishi, Eri Utagawa, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio

    Nucleic acids symposium series (2004)   ( 51 )   129 - 130   2007

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    DOI: 10.1093/nass/nrm065

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  • Synthesis and hybridization properties of oligodeoxynucleotides with long-chain linkers Reviewed

    Kohji Seio, Takeshi Terada, Masahiro Mizuta, Akihiro Ohkubo, Haruhiko Taguchi, Mitsuo Sekine

    HELVETICA CHIMICA ACTA   90 ( 10 )   1946 - 1965   2007

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  • cis-tetrahydrofuran-3,4-diol structure as a key skeleton of new protecting groups removable by self-cyclization under oxidative conditions Reviewed

    Eri Utagawa, Mitsuo Sekine, Kohji Seio

    JOURNAL OF ORGANIC CHEMISTRY   71 ( 20 )   7668 - 7677   2006.9

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    DOI: 10.1021/jo061006v

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  • Incorporation of 2 '-O-methyl-2-thiouridine into oligoribonucleotides induced stable A-form structure Reviewed

    Okamoto, I, K Shohda, K Seio, M Sekine

    CHEMISTRY LETTERS   35 ( 1 )   136 - 137   2006.1

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    DOI: 10.1246/cl.2006.136

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  • Synthesis and biological properties of new phosmidosine analogs having an N-acylsulfamate linkage Reviewed

    H. Taguchi, A. Ohkubo, M. Sekine, K. Seio, H. Kakeya, H. Osada, T. Sasaki

    Nucleosides, Nucleotides and Nucleic Acids   25 ( 4-6 )   647 - 654   2006

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    DOI: 10.1080/15257770600686360

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  • A general method for the synthesis of 2 '-O-cyanoethylated oligoribonucleotides having promising hybridization affinity for DNA and RNA and enhanced nuclease resistance Reviewed

    H Saneyoshi, K Seio, M Sekine

    JOURNAL OF ORGANIC CHEMISTRY   70 ( 25 )   10453 - 10460   2005.12

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    DOI: 10.1021/jo05174.1r

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  • Chemically stabilized phenylboranylidene groups having a dimethoxytrityl group as a colorimetrically detectable protecting group designed for cis-1,2-diol functions of ribonucleosides in the solid-phase synthesis of m(2)(2,2)G5 ' ppT Reviewed

    M Sekine, M Aoyagi, M Ushioda, A Ohkubo, K Seio

    JOURNAL OF ORGANIC CHEMISTRY   70 ( 21 )   8400 - 8408   2005.10

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    DOI: 10.1021/jo051202m

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  • Computational evaluation of intermolecular interactions of a universal base 3-nitropyrrole in stacked dimers and DNA duplexes Reviewed

    K Seio, H Ukawa, K Shohda, M Sekine

    JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS   22 ( 6 )   735 - 746   2005.6

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  • Mild and facile deprotection for the synthesis of oligodeoxynucleotide incorporating a 6-O-ethyl-deoxyguanosine Reviewed

    K Seio, T Negishi, K Negishi, M Sekine

    LETTERS IN ORGANIC CHEMISTRY   2 ( 2 )   179 - 183   2005.3

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  • Synthesis and hybridization properties of 2'-O-methyl-RNA incorporating 3-deazaguanine derivatives.

    Kohji Seio, Takeshi Sasami, Akihiro Ohkubo, Mitsuo Sekine

    Nucleic acids symposium series (2004)   ( 49 )   21 - 22   2005

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    DOI: 10.1093/nass/49.1.21

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  • Synthesis and Properties of New Nucleotide Analogues Possessing Squaramide Moieties as New Phosphate Isosters

    SEIO Kohji, SEIO Kohji, MIYASHITA Takuhei, MIYASHITA Takuhei, SATO Kousuke, SEKINE Mitsuo, SEKINE Mitsuo

    Eur. J. Org. Chem.   2005 ( 24 )   5163 - 5170   2005

  • [Development of new technologies directed toward superfine gene analysis].

    Mitsuo Sekine, Akihiro Ohkubo, Itaru Okamoto, Akio Kobori, Kohji Seio

    Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme   49 ( 17 Suppl )   2978 - 85   2004.12

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  • Synthesis of benzodithiol-2-yl-substituted nucleoside derivatives as lead compounds having anti-bovine viral diarrhea virus activity Reviewed

    K Seio, T Sasaki, K Yanagida, M Baba, M Sekine

    JOURNAL OF MEDICINAL CHEMISTRY   47 ( 21 )   5265 - 5275   2004.10

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    DOI: 10.1021/jm049677d

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  • Synthesis of enol adenosine 5 '-phosphate derivatives by the Perkow reaction of a silylated adenosine 5 '-phosphonate derivative with alpha-halo ketones Reviewed

    T Moriguchi, K Okada, K Seio, M Sekine

    LETTERS IN ORGANIC CHEMISTRY   1 ( 3 )   246 - 248   2004.7

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  • Synthesis and Structural Properties of New Oligonucleotide Analogues Containing a 2’,5’-Internucleotidic Squaryldiamide Linkage Capable of Formation of Watson-Crick and Wobble Base Pairs at the 3’-Downstream Junction Site

    SATO K, TAWARADA R, SEIO K, SEKINE M

    Eur. J. Org. Chem.   ( 10 )   2142 - 2150   2004

  • Synthesis of a biotin-conjugate of phosmidosine O-ethyl ester as a G1 arrest antitumor drug Reviewed

    M. Sekine, K. Okada, K. Seio, T. Obata, T. Sasaki, H. Kakeya, H. Osada

    Bioorganic and Medicinal Chemistry   12 ( 24 )   6343 - 6349   2004

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    DOI: 10.1016/j.bmc.2004.09.037

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  • Structure-activity relationship of phosmidosine: Importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity Reviewed

    M. Sekine, K. Okada, K. Seio, H. Kakeya, H. Osada, T. Sasaki

    Bioorganic and Medicinal Chemistry   12 ( 19 )   5193 - 5201   2004

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    DOI: 10.1016/j.bmc.2004.07.021

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  • Synthesis of Chemically Stabilized Phosmidosine Analogues and the Structure-Activity Relationship of Phosmidosine Reviewed

    M. Sekine, K. Okada, K. Seio, H. Kakeya, H. Osada, T. Obata, T. Sasaki

    Journal of Organic Chemistry   69 ( 2 )   314 - 326   2004

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    DOI: 10.1021/jo0351466

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  • New protected protecting groups for the 5 '-hydroxy group of deoxynucleosides by use of 2-(hydroxymethyl)- and 2-[(methylamino)methyl]benzoyl skeletons and oxidatively cleavable tritylthio and (4-methoxytrityl)thio groups Reviewed

    K Seio, E Utagawa, M Sekine

    HELVETICA CHIMICA ACTA   87 ( 9 )   2318 - 2333   2004

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  • Important factors stabilizing stacking interaction between 3-nitropyrrole and natural nucleobases revealed by ab initio calculations.

    Kohji Seio, Hisashi Ukawa, Koh-ichiro Shohda, Mitsuo Sekine

    Nucleic acids research. Supplement (2001)   ( 3 )   49 - 50   2003

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    DOI: 10.1093/nass/3.1.49

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  • Synthesis and biological properties of stable phosmidosine analogs. Reviewed

    K. Okada, H. Taguchi, K. Seio, H. Kakeya, H. Osada, T. Sasaki, M. Sekine

    Nucleic acids research. Supplement (2001)   ( 3 )   105 - 106   2003

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  • A convenient method for the conversion of beta-thymidine to alpha-thymidine based on TMSOTf-mediated C1 '-epimerization Reviewed

    Y Sato, G Tateno, K Seio, M Sekine

    TETRAHEDRON LETTERS   43 ( 17 )   3251 - 3254   2002.4

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  • Synthesis and Conformational Properties of Dinucleoside Triester Derivatives Involving a Cyclonucleotide Bridge Structure Reviewed

    Sekine M, Kurasawa O, Shoda K, Seio K, Wada T

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   1989 - 1999   2001

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  • Synthesis and properties of a new oligonucleotide analogue containing an internucleotide squaryl amide linkage.

    Sato K, Seio K, Sekine M

    Nucleic acids symposium series   1   121 - 122   2001

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  • A new coupling method for the synthesis of oligodeoxyribonucleotides based on protection by protonation of nucleoside bases.

    A. Ohkubo, K. Seio, M. Sekine

    Nucleic acids research. Supplement (2001)   ( 1 )   77 - 78   2001

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    DOI: 10.1093/nass/1.1.77

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  • Fabrication of directly synthesized DNA chip using photolithography for rapid and parallel gene analysis Reviewed

    K Takahashi, K Seio, M Sekine, O Hino, M Esashi

    TRANSDUCERS '01: EUROSENSORS XV, DIGEST OF TECHNICAL PAPERS, VOLS 1 AND 2   326 - 329   2001

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MISC

  • Synthesis of 5-methyluridine derivatives with sulfonamide or sulfonate modifications on the 2 ́ hydroxyl group and evaluation of their ability to form duplex chains

    瀧川駿太朗, 友利貴人, 植草宏哉, 正木慶昭, 清尾康志

    日本化学会春季年会講演予稿集(Web)   104th   2024

  • Synthesis and evaluation of a thymidine dimer with an extended backbone at five prime position

    立花茂載, 大西里絵, 正木慶昭, 清尾康志

    日本化学会春季年会講演予稿集(Web)   104th   2024

  • Synthesis and properties of oligonucleotides having substituted 2 ́-O, 3 ́-C-bridged [3.2.0]bicycloarabinonucleoside

    田平彩乃, 若月駿介, 清尾康志, 正木慶昭

    日本化学会春季年会講演予稿集(Web)   104th   2024

  • Synthesis and properties of oligonucleotides conjugated with sugar ligands for selective cell delivery

    島村大輝, 有江嶺美, 金山朱里, 宮内彩, 清尾康志, 正木慶昭

    日本化学会春季年会講演予稿集(Web)   104th   2024

  • Synthesis and antisense properties of gapmers incorporating sulfonamide-backbone

    清尾康志, 大西里絵, 立花茂載, 正木慶昭

    日本核酸医薬学会年会講演要旨集(CD-ROM)   8th   2023

  • Effects of methylene insertion in backbone of antisense oligonucleotides on RNase H mediated cleavage of mismatched duplexes

    田平彩乃, 服部詩萌里, 清尾康志, 正木慶昭

    日本核酸医薬学会年会講演要旨集(CD-ROM)   8th   2023

  • The effects of “X-CE”, modified nucleotides with various substituents via 2’-O-carbamoylethyl linker, on the reduction of toxicity and mRNA knockdown for Gapmer antisense oligonucleotides

    入江雅彦, 細沢友紀, 西口由菜, 廣瀬優太, 加賀谷賢太, 日高夕貴, 窪山剛之, 正木慶昭, 清尾康志, 入山友輔

    日本核酸医薬学会年会講演要旨集(CD-ROM)   8th   2023

  • Synthesis and properties of oligonucleotides containing 5 ́-deoxy-5 ́-hydroxymethylthymidine and 3 ́-deoxy-3 ́-hydroxymethylthymidine

    正木慶昭, 正木慶昭, 田平彩乃, 服部詩萌里, 清尾康志

    日本化学会春季年会講演予稿集(Web)   102nd   2022

  • Study of the synthesis of thymidine derivative whose base and 5 ́ position are linked through sulfonamide backbone

    金川峻幸, 立花茂載, 大西里絵, 正木慶昭, 正木慶昭, 清尾康志

    日本化学会春季年会講演予稿集(Web)   102nd   2022

  • Synthesis of Sulfonamide linkage-Containing Oligonucleotides and Evaluation of antisense activity

    大西里絵, 清尾康志, 正木慶昭, 正木慶昭, 関谷彰太, 枝村亘

    日本化学会春季年会講演予稿集(Web)   102nd   2022

  • Development of New Methods for Synthesis of Artificial Nucleic Acids having Various Functional Groups

    Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   72 ( 8 )   899 - 909   2014.8

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  • Base recognition of gap sites in DNA-DNA and DNA-RNA duplexes by short oligonucleotides

    Ken Yamada, Yohsuke Esaka, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Bioorganic & Medicinal Chemistry Letters   23 ( 11 )   3448 - 3451   2013

  • SYNTHESIS AND PROPERTIES OF OLIGONUCLEOTIDES HAVING 5 &apos;-TERMINAL 2,2,7-TRIMETHYLGUANOSINE CAP ANALOGUES

    Akihiro Ohkubo, Akira Yokouchi, Ken Yamada, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

    NUCLEIC ACID THERAPEUTICS   21 ( 5 )   A39 - A40   2011.10

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  • 2′-O-[(N-メチルカルバモイル)エチル]ウリジンを組み込んだRNAオリゴマーの合成と性質

    山田剛史, 岡庭夏己, 角田浩佑, 大窪章寛, 清尾康志, 関根光雄

    日本化学会講演予稿集   91st ( 3 )   2011

  • 2′水酸基修飾アンチセンスオリゴヌクレオチドの合成と筋ジストロフィーを対象としたエキソンスキッピング評価

    山田剛史, 岡庭夏己, 角田浩佑, 大窪章寛, 清尾康志, 関根光雄

    日本RNA学会年会要旨集   12th   2010

  • Development of a new strategy for the synthesis of oligonucleotides 5’-adenylated via a diphosphate linkage

    大窪章寛, 西野雄大, 野間靖弘, 桑山靖和, 角田浩佑, 清尾康志, 関根光雄

    日本化学会講演予稿集   89th ( 2 )   2009

  • プリンヌクレオシドへの2′-O-メチルカルバモイルエチル基の導入検討

    山田剛史, 角田浩佑, 大窪章寛, 清尾康志, 関根光雄

    日本RNA学会年会要旨集   11th   2009

  • Binding of MutS protein to oligonucleotides containing a methylated- or an ethylated guanine residue, and correlation with mutation frequency

    Kentro Taira, Shintaro Nakamura, Khota Nakano, Daisuke Maehara, Keinosuke Okamoto, S. Arimoto, D. Loakes, L. Worth, Jr, R. M. Schaaper, Kohji Seio, Mitsuo Sekine, Kazuo Negishi, Tomoe Negishi

    Mutation Research   640   107 - 112   2008

  • Synthesis and fluorescent properties of bi- and tricyclic 4-N-carbamoyldeoxycytidine derivatives

    K.Miyata, R.Mineo, R.Tamamushi, M.Mizuta, A.Ohkubo, H.Taguchi, K.Seio, T.Santa

    J Org Chem   72 ( 1 )   102 - 108   2007

  • 2’末端に極性をもった官能基を導入した修飾核酸の合成と性質

    山田剛史, 山田剛史, 實吉尚郎, 大窪章寛, 大窪章寛, 清尾康志, 清尾康志, 関根光雄, 関根光雄

    アンチセンスシンポジウム講演要旨集   17th   2007

  • 1,1-Dihydroperoxycyclododecaneas a new, crystalline non-hygroscopic oxidizer for the chemical synthesis of oligodeoxyribonucleotides

    Hisao Saneyoshi, Kenichi Miyata, Kohji Seio, Mitsuo Sekine

    TETRAHEDRON LETTERS   47 ( 50 )   8945 - 8947   2006.12

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  • Synthesis of 2 &apos;-O-methyl-RNAs incorporating a 3-deazaguanine, and UV melting and computational studies on its hybridization properties

    Kohji Seio, Takeshi Sasami, Ryuya Tawarada, Mitsuo Sekine

    NUCLEIC ACIDS RESEARCH   34 ( 16 )   4324 - 4334   2006.9

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  • Conformational studies of 4-N-carbamoyldeoxycytidine derivatives and synthesis and hybridization properties of oligodeoxyribonucleotides incorporating these modified bases

    Kenichi Miyata, Akio Kobori, Ryuji Tamamushi, Akihiro Ohkubo, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2006 ( 16 )   3626 - 3637   2006.8

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  • Improved synthesis of oligonucleotides containing 2-thiouridine derivatives by use of diluted iodine solution

    Okamoto, I, K Seio, M Sekine

    TETRAHEDRON LETTERS   47 ( 4 )   583 - 585   2006.1

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  • DNA Synthesis without Base Protection Using the Phosphoramidite Approach

    Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Current Protocol in Nucleic Acid Chemistry   1 ( 3.15 )   1 - 20   2006

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  • Synthesis and properties of a new fluorescent bicyclic 4-N-carbamoyldeoxycytidine derivative

    K.Miyata, R.Tamamushi, A.Ohkubo, H.Taguchi, K.Seio, T.Santa, M.Sekine

    Org Lett   8 ( 8 )   1545 - 1548   2006

  • Synthesis of Deoxycytidine Derivative and Their Use for the Selective Photo Crosslinking with 5-Methylcytosine

    Haruhiko Taguchi, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Nucleic Acids Res. Symposium Ser.   50   57 - 58   2006

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  • Synthesis and Properties of Artificial Base Pairs by Use of Halogen Bonds

    Ryuta Tawarada, Kohji Seio, Mitsuo Sekine

    Nucleic Acids Res. Symposium Ser.   50   121 - 122   2006

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  • Synthesis and Properties of DNA Oligomers Containing 2'-Deoxycytidine-N-Oxide

    Hirosuke Tsunoda Akihiro Ohkubo, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

    Nucleic Acids Res. Symposium Ser.   50   189 - 190   2006

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  • Use of ferrocene scaffolds as pendant groups in hairpin-type pyrrole-imidazole polyamide molecules showing sequence-selective binding to DNA duplexes

    K Seio, M Mizuta, T Terada, M Sekine

    JOURNAL OF ORGANIC CHEMISTRY   70 ( 25 )   10311 - 10322   2005.12

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  • Synthesis of oligodeoxyribonucleotides containing hydroxymethylphosphonate bonds in the phosphoramidite method and their hybridization properties

    A Ohkubo, K Aoki, Y Ezawa, Y Sato, H Taguchi, K Seio, M Sekine

    TETRAHEDRON LETTERS   46 ( 51 )   8953 - 8957   2005.12

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  • Convenient synthesis of N-unprotected deoxynucleoside 3 '-phosphoramidite building blocks by selective deacylation of N-acylated species and their facile conversion to other N-functionalized derivatives

    A Ohkubo, K Sakamoto, K Miyata, H Taguchi, K Seio, M Sekine

    ORGANIC LETTERS   7 ( 24 )   5389 - 5392   2005.11

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  • Synthesis and conformational analysis of 4-N-carbamoyldeoxycytidine derivatives.

    K Miyata, R Tamamushi, A Ohkubo, H Taguchi, K Seio, M Sekine

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   229   U560 - U560   2005.3

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  • O-selectivity and utility of phosphorylation mediated by phosphite triester intermediates in the N-unprotected phosphoramidite method.

    A Ohkubo, H Taguchi, K Seio, M Sekine

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   229   U559 - U560   2005.3

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  • 4,5-bis(ethoxycarbonyl)-[1,3]dioxolan-2-yl as a new orthoester-type protecting group for the 2 '-hydroxyl function in the chemical synthesis of RNA

    B Karwowski, K Seio, M Sekine

    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS   24 ( 5-7 )   1111 - 1114   2005

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  • Analysis by Use of Protected Oligonucleotides Probes.

    A. Ohkubo, R. Kasuya, K. Sakamoto, H. Taguchi, K. Seio, M. Sekine

    Nucleic Acids Symposium Ser.   49   19 - 20   2005

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  • A new protecting group for the 5 '-hydroxyl group having O-S single bond oxidatively cleavable under mild conditions

    E Utagawa, K Seio, M Sekine

    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS   24 ( 5-7 )   927 - 929   2005

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  • Development of New N-Unprotected Phosphoramidite Building Blocks Having a Silyl-Type Linker

    A. Ohkubo, K. Aoki, H. Taguchi, K. Seio, M. Sekine

    Nucleic Acids Symposium Ser.   49   127 - 128   2005

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  • Synthesis of 2'- or 3'-O-Heteroaryl Substituted Nucleic Acid Derivatives and Their Biological Properties

    H. Taguchi, T. Narita, K. Seio, M. Sekine

    Nucleic Acids Symposium Ser.   49   113 - 114   2005

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  • SNPs Analysis by Use of Oligonucleotides Containing 2'-O-Methyl-2-thiouridines.

    I. Okamoto, K. Seio, M. Sekine

    Nucleic Acids Symposium Ser.   49   123 - 124   2005

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  • Synthesis and hybridization affinity of oligodeoxyribonucleotides incorporating 4-N-(N-arylcarbamoyl)deoxycytidine derivatives

    K Miyata, R Tamamushi, A Ohkubo, H Taguchi, K Seio, M Sekine

    TETRAHEDRON LETTERS   45 ( 51 )   9365 - 9368   2004.12

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  • O-selectivity and utility of phosphorylation mediated by phosphite triester intermediates in the N-unprotected phosphoramidite method

    A Ohkubo, Y Ezawa, K Seio, M Sekine

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   126 ( 35 )   10884 - 10896   2004.9

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  • Synthesis and properties of a pyrrole-imidazole polyamide having a ferrocene dicarboxylic amide linker

    K Seio, M Mizuta, T Terada, M Sekine

    TETRAHEDRON LETTERS   45 ( 36 )   6783 - 6786   2004.8

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  • Fine-tuning of acid susceptibility of 4,4 '-dimethoxytrityl ether derivatives by a methoxy group introduced via a styryl substituent

    K Seio, T Sasaki, M Sekine

    LETTERS IN ORGANIC CHEMISTRY   1 ( 2 )   159 - 162   2004.4

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  • Synthesis and stability of 1-phenylethenyl phosphate derivatives and their phosphoryl transfer activity

    T Moriguchi, K Okada, K Seio, M Sekine

    LETTERS IN ORGANIC CHEMISTRY   1 ( 2 )   140 - 144   2004.4

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  • A new approach for pyrophosphate bond formation starting from phosphoramidite derivatives by use of 6-trifluoromethyl-1-hydroxybenzotriazole-mediated O-N phosphoryl migration

    A Ohkubo, K Aoki, K Seio, M Sekine

    TETRAHEDRON LETTERS   45 ( 5 )   979 - 982   2004.1

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  • A new strategy for the synthesis of oligodeoxynucleotides directed towards perfect O-selective internucleotidic bond formation without base protection

    A Ohkubo, K Seio, M Sekine

    TETRAHEDRON LETTERS   45 ( 2 )   363 - 366   2004.1

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  • Synthesis and Base Recognition Ability of Oligoribonucleotides Incorporating 2-O-methyl-3-Deazaguanosine

    Kohji Seio, Takeshi, Sasami Mitsuo Sekine

    Nucleic Acids Symp. Series   48   65 - 66   2004

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  • Properties of Ferrocene-polyamide Compounds as Redox Active DNA binding Molecules toward SNPs Detection

    Masahiro Mizuta, Takeshi Terada, Kohji Seio, Mitsuo Sekine

    Nucleic Acids Symp. Series   48   237 - 238   2004

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  • A new route to 2 '-O-alkyl-2-thiouridine derivatives via 4-o-protection of the uracil base and hybridization properties of oligonucleotides incorporating these modified nucleoside derivatives

    Okamoto, I, K Shohda, K Seio, M Sekine

    JOURNAL OF ORGANIC CHEMISTRY   68 ( 26 )   9971 - 9982   2003.12

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  • Proton-block strategy for the synthesis of oligodeoxynucleotides without base protection, capping reaction, and P-N bond cleavage reaction

    M Sekine, A Ohkubo, K Seio

    JOURNAL OF ORGANIC CHEMISTRY   68 ( 14 )   5478 - 5492   2003.7

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  • Enhanced stereoselectivity in internucleotidic bond formation by the use of the chiral ribose moiety of thymidine

    K Seio, K Kumura, JC Bologna, M Sekine

    JOURNAL OF ORGANIC CHEMISTRY   68 ( 10 )   3849 - 3859   2003.5

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  • Synthesis of TMG-capped RNA-DNA chimeric oligonucleotides

    M Sekine, M Ushioda, T Wada, K Seio

    TETRAHEDRON LETTERS   44 ( 8 )   1703 - 1707   2003.2

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  • Important factors stabilizing stacking interaction between 3-nitropyrrole and natural nucleobases revealed by ab intio calculations

    Kohji Seio, Hisashi Ukawa, Koh-ichiro Shohda, Mitsuo Sekine

    Nucleic Acids Res. Suppl.   3   49 - 50   2003

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  • Enhanced Stereoselectivity in Internucleotide Linkage Formation by the Effective Use of Intrinsically Chiral Ribose Miety of Nucleoside.

    K. Seio, K. Kumura, M. Sekine

    J. Org. Chem.   68   3849 - 3859   2003

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  • A Proton-Block Strategy in the Phosphoramidite Approach: A New N-Unprotected Method for the Synthesis of Oligodeoxynucleotides Based on the Principle of Simple Acid-Base Reactions.

    M. Sekine, A. Ohkubo, K. Seio

    J. Org. Chem.   68   5478 - 5492   2003

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  • Squaryl group as a new mimic of phosphate group in modified oligodeoxynucleotides: Synthesis and properties of new oligodeoxynucleotide analogues containing an internucleotidic squaryldiamide linkage

    K Sato, K Seio, M Sekine

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   124 ( 43 )   12715 - 12724   2002.10

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  • First synthesis and anticancer activity of phosmidosine and its related compounds

    T Moriguchi, N Asai, K Okada, K Seio, T Sasaki, M Sekine

    JOURNAL OF ORGANIC CHEMISTRY   67 ( 10 )   3290 - 3300   2002.5

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  • A photochemical/chemical direct method of synthesizing high-performance deoxyribonucleic acid chips for rapid and parallel gene analysis

    K Takahashii, K Seio, M Sekine, O Hino, M Esashi

    SENSORS AND ACTUATORS B-CHEMICAL   83 ( 1-3 )   67 - 76   2002.3

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  • Substituent and solvent effects of TMS triflate mediated C1 ' epimerization of beta-thymidine to alpha-thymidine

    Y Sato, G Tateno, K Seio, M Sekine

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 1 )   87 - 93   2002.1

  • A new method for the synthesis of oligodeoxyribonucleotides containing 4-N-alkoxycarbonyldeoxycytidine derivatives and their hybridization properties

    A Kobori, K Miyata, M Ushioda, K Seio, M Sekine

    JOURNAL OF ORGANIC CHEMISTRY   67 ( 2 )   476 - 485   2002.1

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  • A new silyl ether-type linker useful for the automated synthesis of oligonucleotides having base-labile protective groups

    A Kobori, K Miyata, M Ushioda, K Seio, M Sekine

    CHEMISTRY LETTERS   ( 1 )   16 - 17   2002.1

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  • Unique participation of unprotected internucleotidic phosphodiester residues on unexpected cleavage reaction of the Si-O bond of the diisopropylsilandiyl group used as a linker for the solid-phase synthesis of 5 '-terminal guanylated oligodeoxynucleotides

    M Ushioda, M Kadokura, T Moriguchi, A Kobori, M Aoyagi, K Seio, M Sekine

    HELVETICA CHIMICA ACTA   85 ( 9 )   2930 - 2945   2002

  • A new strategy for the synthesis of oligodeoxynucleotides in the phosphoramidite method without base protection via phosphite intermediates

    Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

    Nucleic Acids Research Supplement   2   29 - 30   2002

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  • A new protecting group for 5'-hydroxyl function of nucleitides in oligonucleotide snthesis without acid treatment utilizing unique properties of tritylthio group

    Kohji Seio Eri Utagawa, Mitsuo Sekine

    Nucleic Acid Research Supplement   2   27 - 28   2002

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  • A new protecting group for 5'-hydroxyl function of nucleotides in oligonucleotide synthesis without acid treatment utilizing unique properties of tritylthio group

    Kohji Seio Eri Utagawa, Mitsuo Sekine

    Nucleic Acids Research Supplement   2   27 - 28   2002

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  • A New Finding in Connection with Side Reaction Associated with 5'-Terminal Pyrophosphorylation of Oligodeoxynucleotides on Polymer Supports: Selective Si-O Bond Cleavage by Strong Nucleophilicity of 4-Nitro-6-(triluoromethyl)-1H-1,2,3-benzotriazol-1-ol

    M. Ushioda M, Kadokura, T. Moriguchi, A. Kobori, M. Aoyagi, K. Seio, M. Sekine

    Helv. Chim. Acta.   85   2930 - 2945   2002

  • Computational Analysis of Stacking Interactions betwee 3-Nitropyrrole and Natural Nucleobases

    Hisashi Ukawa, Kohji Seio, Mitsuo Sekine

    Nucleic Acids Research Supplement   2   173 - 174   2002

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  • Hybridization Ability and Base Pair Geometry of Modified Deoxycytidine Derivatives Having a 4-N-Carbamoyl Group

    Kenichi Miyata Akio Kobori, Kohji Seio, Mitsuo Sekine

    Nucleic Acids Research Supplement   2   161 - 162   2002

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  • Solid-phase synthesis of a 5 '-terminal TMG-capped trinucleotide block of U1 snRNA

    M Kadokura, T Wada, K Seio, T Moriguchi, J Huber, R Luhrmann, M Sekine

    TETRAHEDRON LETTERS   42 ( 50 )   8853 - 8856   2001.12

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  • Synthesis of pentathymidylate using a 4-monomethoxytritylthio (MMTrS) group as a 5 '-hydroxyl protecting group: toward oligonucleotide synthesis without acid treatment

    K Seio, M Sekine

    TETRAHEDRON LETTERS   42 ( 49 )   8657 - 8660   2001.12

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  • Total synthesis of agrocin 84 and phosmidosine as naturally occurring nucleotidic antibiotics having P-N bond linkages

    M Sekine, T Moriguchi, T Wada, K Seio

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   59 ( 11 )   1109 - 1120   2001.11

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    DOI: 10.5059/yukigoseikyokaishi.59.1109

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  • Essential factors for stabilization of the predominant C3 '-endo conformation in dinucleoside phosphotriester derivatives with cyclonucleotide bridge structures at the downstream 3 '-position

    M Sekine, O Kurasawa, K Shohda, K Seio, T Wada

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 10 )   1989 - 1999   2001.5

  • Binding Specificities of the Mismatch Binding Protein, MutS, to Oligonucleotides Containing Modified bases

    K. Negishi, D. Maehara, S. Nakamura, D. Loakes, l. Worth, Jr. R. M. Schaaper, K. Seio, M, Sekine T. Negishi

    Nuceic Acids Research Supplement No1   221 - 222   2001

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  • Synthesis and Properties of a New Nucleotide Analogue Containing Squaryl Group

    Kousuke Sato, Kohji Seio, Mitsuo Sekine

    Nuceic Acids Research Supplement No1   121 - 122   2001

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  • A New Coupling Method for the Synthesis of Oligodeoxyribonucleotides Based on Protection by Protonation of Nnucleoside Bbases

    A. Ohkubo, K. Seio, M. Sekine

    Nuceic Acids Research Supplement No1   77 - 78   2001

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  • Substituent and Solvent Effects of TMS-triflate mediated C1'-Epimerization of beta-Thymidine to alpha-Thymidine

    Yuichi Sato, Gohsuke, Tateno, Kohji Seio, Mitsuo Sekine

    Eur. J. Org. Chem.   4583 - 4593   2001

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  • Synthesis and properties of oligonucleotides having a phosphorus chiral center by incorporation of conformationally rigid 5 '-cyclouridylic acid derivatives

    M Sekine, O Kurasawa, K Shohda, K Seio, T Wada

    JOURNAL OF ORGANIC CHEMISTRY   65 ( 20 )   6515 - 6524   2000.10

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  • Synthesis and properties of 2 '-O-methyl-2-thiouridine and oligoribonucleotides containing 2 '-O-methyl-2-thiouridine

    K Shohda, Okamoto, I, T Wada, K Seio, M Sekine

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   10 ( 16 )   1795 - 1798   2000.8

  • Synthesis of 4-thiouridine, 6-thioinosine, and 6-thioguanosine 3 ',5 '-O-bisphosphates as donor molecules for RNA ligation and their application to the synthesis of photoactivatable TMG-capped U1 snRNA fragments

    M Kadokura, T Wada, K Seio, M Sekine

    JOURNAL OF ORGANIC CHEMISTRY   65 ( 17 )   5104 - 5113   2000.8

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  • Synthesis and antitumor activities of phosmidosine A and its N- acetylated derivative

    Tomohisa Moriguchi, Norio Asai, Takeshi Wada, Kohji Seio, Takuma Sasaki, Mitsuo Sekine

    Tetrahedron Letters   41 ( 31 )   5881 - 5885   2000.7

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    DOI: 10.1016/S0040-4039(00)00926-6

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  • Synthesis and properties of oligodeoxynucleotides incorporating a conformationally rigid uridine unit having a cyclic structure at the 5 '-terminal site

    M Sekine, O Kurasawa, K Shohda, K Seio, T Wada

    JOURNAL OF ORGANIC CHEMISTRY   65 ( 12 )   3571 - 3578   2000.6

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  • Synthesis and properties of oligothymidylates incorporating an artificial bend motif

    K Seio, T Wada, M Sekine

    HELVETICA CHIMICA ACTA   83 ( 1 )   162 - 180   2000

  • Chemical synthesis of hydroxymethylphosophnate α-DNA

    KOHJI SEIO

    Nucleic Acids Sym. Ser.   44   31 - 32   2000

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  • Synthesis of N-labeled peptidyl AMP

    H Narita, T Moriguchi, K Seio, M Sekine, H Miyaguchi, K Sakamoto, S Yokoyama

    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS   19 ( 10-12 )   1993 - 2003   2000

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  • Solid-phase synthesis of deoxyribonucleotides having a cap structure analog

    KOHJI SEIO

    Nucleic Acids Symp. Ser.   44   123 - 124   2000

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  • Synthesis of artificially bent oligonucleotides by incorporation of conformationally rigid 5 '-cyclouridylic acid derivatives

    M Sekine, O Kurasawa, K Seio, K Shohda, T Wada

    NUCLEOSIDES & NUCLEOTIDES   18 ( 6-7 )   1163 - 1168   1999

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  • Synthesis of artificially bent oligonucleotides by incorporation of conformationally rigid 5 '-cyclouridylic acid derivatives

    M Sekine, O Kurasawa, K Seio, K Shohda, T Wada

    NUCLEOSIDES & NUCLEOTIDES   18 ( 6-7 )   1163 - 1168   1999

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  • The Chemical Synthesis of Hypermethylated Capped RNA on Polymer Supports

    M. Sekine, M, Kadokura T, Satoh T, Wada K. Seio

    J. Mol. Science   15   318   1999

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  • Chemical synthesis and properties of conformationally fixed diuridine monophosphates as building blocks of the RNA turn motif

    K Seio, T Wada, K Sakamoto, S Yokoyama, M Sekine

    JOURNAL OF ORGANIC CHEMISTRY   63 ( 5 )   1429 - 1443   1998.3

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  • Synthesis and properties of conformationally rigid cyclouridylic acids having covalent bonding linkers between the uracil 5-position and the 5'-phosphate group

    K Seio, O Kurasawa, T Wada, K Sakamoto, S Yokoyama, M Sekine

    NUCLEOSIDES & NUCLEOTIDES   16 ( 7-9 )   1023 - 1032   1997

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  • Chemical synthesis of a 5'-terminal TMG-capped triribonucleotide m(3)(2,2,7)G(5')pppAmpUmpA of U1 RNA

    M Sekine, M Kadokura, T Satoh, K Seio, T Wada, U Fischer, Sumpter, V, R Luhrmann

    JOURNAL OF ORGANIC CHEMISTRY   61 ( 13 )   4412 - 4422   1996.6

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  • Chemical synthesis and conformational properties of a new cyclouridylic acid having an ethylene bridge between the uracil 5-position and 5'-phosphate group

    K Seio, T Wada, K Sakamoto, S Yokoyama, M Sekine

    JOURNAL OF ORGANIC CHEMISTRY   61 ( 4 )   1500 - 1504   1996.2

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  • Synthesis and properties of conformationally rigid cyclouridylic acid having a covalent bonding linker between the uracil 5-position and the 5′-phosphate group

    Kohji Scio, Takeshi Wada, Kensaku Sakamoto, Shigeyuki Yokoyama, Mitsuo Sekine

    Tetrahedron Letters   36 ( 52 )   9515 - 9518   1995.12

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  • Synthesis of oligonucleotide having a bent structure by incorporation of an interresidually cyclized uridylyl(3'-5')uridine unit

    KOHJI SEIO

    Nucleic Acids Symp. Ser.   34   181 - 182   1995

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  • CHEMICAL SYNTHESIS AND PROPERTIES OF AN INTERRESIDUALLY CYCLIZED URIDYLYL(3'-5')URIDINE AS A MODEL OF TRANSFER-RNA U-TURN STRUCTURE HAVING A SHARP BEND

    M SEKINE, K SEIO, T WADA, K SAKAMOTO, S YOKOYAMA

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   116 ( 10 )   4469 - 4470   1994.5

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  • Chemical synthesis of the 5'-terminal structure of U1 RNA

    KOHJI SEIO

    Nucleic Acids Symp. Ser.   31   61 - 62   1994

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  • SYNTHESIS AND PROPERTIES OF N-TRITYLTHIO NUCLEOSIDE DERIVATIVES AND REDUCTIVE REMOVAL OF THE TRITYLTHIO GROUP BY USE OF TRIBUTYLTIN HYDRIDE AND TRIS(TRIMETHYLSILYL)SILANE

    M SEKINE, K SEIO

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 24 )   3087 - 3093   1993.12

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  • SYNTHESIS OF URIDYLYL (3'-5') URIDINE DERIVATIVES CONTAINING 5-(METHYLAMINO-METHYL)URIDINE AS A MODIFIED NUCLEOSIDE FOUND FROM ESCHERICHIA-COLI MINOR TRANSFER RNA(ARG)

    M SEKINE, K SEIO, T SATOH, K SAKAMOTO, S YOKOYAMA

    NUCLEOSIDES & NUCLEOTIDES   12 ( 3-4 )   305 - 321   1993

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Research Projects

  • 真核生物におけるppGppの機能解明を目指した分子プローブの開発

    Grant number:21H02075  2021.4 - 2024.3

    日本学術振興会  科学研究費助成事業  基盤研究(B)

    清尾 康志, 増田 真二

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    Grant amount:\17290000 ( Direct Cost: \13300000 、 Indirect Cost:\3990000 )

    グアノシンを出発原料として用い、2', 3'-水酸基の保護を経て2'水酸基がらビオチンリンカーを伸長したグアノシン保護体との合成とその3', 5'水酸基のビスピロリン酸化を達達成し、予定通り2'位にビオチンリンカーを有するppGpp誘導体の合成法を確立して。また、アビジン単体へのこの誘導体の固定、シロイヌナズナの細胞からのタンパク質含有抽出液の作製および、抽出液中のタンパク質の質量分析による網羅的同定法の予備検討そ実施し、ppGpp結合タンパク質を同定するための実験に必要な試料および同定法を確立した。

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  • インターヌクレオチド結合をスルホンアミドに置換した架橋型アンチセンス核酸の合成

    Grant number:20K21245  2020.7 - 2023.3

    日本学術振興会  科学研究費助成事業  挑戦的研究(萌芽)

    清尾 康志

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    Grant amount:\6500000 ( Direct Cost: \5000000 、 Indirect Cost:\1500000 )

    昨年度合成した塩基部にヒドロキシプロピル基、糖部にイソブチルオキシスルホニル基を有する誘導体の環化反応を行うための合成反応を行った。まずヒドロキシプロピル基水酸基をメシル化しアジ化ナトリウムとの反応によりアジドプロピル基に変換するとともに色ブチル基の脱保護を行った。ついで生じたスルホナド基をスルホニルイミダゾリル基に変換し環化反応の検討を行った。環化反応としてはアジド基を還元すると同時に分子内で環化反応が進行する反応を検討し、約30%の収率で環化生成物を得ることができた。
    環化生成物についてそのコンホメーションを1H-NMRで解析したところ、東部の配座はS型に4'-5'炭素の回りの配座はtransに固定化されていることが分かった。

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  • シュライバーサイト由来リン化学種の反応を起源とする生命分子の生成反応

    Grant number:17H05230  2017.4 - 2019.3

    日本学術振興会  科学研究費助成事業  新学術領域研究(研究領域提案型)

    清尾 康志

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    Grant amount:\7410000 ( Direct Cost: \5700000 、 Indirect Cost:\1710000 )

    生体分子の多くはリンを含み、何故リンが生命の必須元素になったのかを理解することは生命起源を知る上で重要である。冥王代の地球ではリンはシュライバーサイト[Fe3P]として存在していた。Fe3Pは水と反応し様々な還元的リン化学種を生成する。また、リボヌクレオチドと反応し、2', 3'-AMPも生成する。本研究では、冥王代のFe3Pの役割をさらに解明するためにFe3PやFe3P由来リン化学種と様々な生体分子との反応を調べた。特に、アミノ酸、糖、グリセルアルデヒド等との反応生成物を解析し、これら生成物から複雑な生命分子や代謝反応が誕生した可能性を明らかにするための実験を行った。
    その結果、シュライバーサイトから生成するピロ亜リン酸(H4PO5)はpH9程度の弱アルカリ性の条件下、セリン、チロシン、トレオニンなどのアミノ酸の側鎖に存在する水酸基、リボース、グリセルアルデヒドなどの炭水化物の水酸基と反応し、対応する亜リン酸モノエステルを与えることを31P-NMRにより明らかにした。
    また、生成した亜リン酸エステルが酸化されてリン酸エステルに変換される可能性を検証するために、種々の酸化反応を検討したところ、ペルオキソ二硫酸カリウムなどの酸化剤やパラジウムなどの金属触媒の存在下、亜リン酸モノエステルからリン酸エステルが生成することを明らかにした。
    以上の結果より、冥王代において比較的穏和な条件下、シュライバーサイト由来リン化学により、様々な生体分子の亜リン酸モノエステルやリン酸エステルが生成する可能性が示された。

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  • Investigation of biological basis of GSK3beta-targeted therapy and its translation to colorectal cancer treatment

    Grant number:15H04928  2015.4 - 2018.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    MINAMOTO Toshinari, OHTA Tetsuo, SOGA Tomoyoshi, SEIO Kohshi, DOMOTO Takahiro

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    Grant amount:\16640000 ( Direct Cost: \12800000 、 Indirect Cost:\3840000 )

    We explored the biological role of glycogen synthase kinase (GSK)3β in colorectal cancer (CRC) progression by focusing on the distinct metabolic profile and micro(mi)-RNA. Expression of GSK3β was increased in 70% of clinical CRC tumors, which was associated inversely with expression of tumor suppressive let-7 miRNA but not with activation of K-ras or Src oncoprotein. Metabolic analysis of GSK3β in CRC cells and tumors found that GSK3β was responsible for tumor-promoting aberrant metabolism. For translation of GSK3β-targeted therapy to cancer treatment, we also conducted preliminary studies on cancer therapeutic effects of GSK3β-inhibiting seed compounds.

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  • 酸化還元反応と共役する冥王代ヌクレオチド生成反応

    Grant number:15H01062  2015.4 - 2017.3

    日本学術振興会  科学研究費助成事業  新学術領域研究(研究領域提案型)

    清尾 康志

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    Grant amount:\7930000 ( Direct Cost: \6100000 、 Indirect Cost:\1830000 )

    本研究では、冥王代におけるヌクレオシドの生成のメカニズムとして、酸化剤と還元剤とか反応うすることに共役して、リボースと核酸塩基とが縮合する反応を考え、有機化学反応の一種である光延反応をモデル化合物として検討そ行った。その結果、光延試薬としてトリブチルホスフィンとアゾジカルボニルジピペリジンを用いて、水酸基を保護したデオキシリボースと種々、のプリン塩基もしくはピリミジン塩基を反応させることで効率よくデオキシヌクレオシドが生成することが分かった。また、上記の光延試薬の他にも冥王代地球環境下で存在しえた、ホスフィナイトやマレイン酸を用いて反応を行った場合も同様に光延反応が進行することが分かり、冥王代においても適切な酸化剤と還元剤の組み合わせが存在すれば、類似の反応によりヌクレオシドが生成する可能性が示唆された。
    また、リボースが活性化されるもうひとつのメカニズムとして、冥王代に存在したシュライバーサイトおよびシュライバーサイトから生成する還元的リン化学種が反応した可能性を考え、シュライバーサイトから生成するジホスホン酸と種々の生命分子前駆体との反応を検討した。その結果、反応系のpHを9程度の弱アルカリ性に保つことで、ヌクレオシド、リボース、グリセロールなどの水酸基が亜リン酸化されることが分かった。さらに、検討を進めたところ、チロシン、セリン、スレオニンなどの側鎖も同様の条件で亜リン酸化されることが分かった。
    これらの結果から、冥王代地球環境に存在したと予想される還元的なリン化学種が生命分子の分子進化に関与していることが示唆された。

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  • Enzymatic synthesis of site specifically isotope labelled RNA

    Grant number:15K13738  2015.4 - 2017.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Exploratory Research

    Seio Kohji

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    Grant amount:\3900000 ( Direct Cost: \3000000 、 Indirect Cost:\900000 )

    We studied the enzymatic incorporation of base- or sugar-modified ribonucleoside triphosphates by T7-RNA polymerase to develop the future technology to synthesize isotope-labeled RNA enzymatically. We tested 6-O-nitrobenzylguanosine and 4-O-nitrobenzyluridine triphosphates as the substrates of T7-RNA polymerase. However, it was revealed that both nucleoside triphosphates acted as inhibitor of the polymerase when concentrations of the nucleoside triphosphates were high. On the contrary, as the sugar modified nucleoside triphosphates, we tested 2'-O-carbamoyluridine triphosphate as the substrate or T7-RNA polyerase and found that this modified nucleoside triphosphate could be incorporated into RNA strand enzymatically. This result suggested that the carmaoyl-modified nucleoside triphosphate can be used for the enzymatic synthesis chemically modified functional RNAs such as RNA aptamers.

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  • Chemically modified DNAs cotrolled by triplex forming oligodeoxynucleotides

    Grant number:26288075  2014.4 - 2017.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    Seio Kohji

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    Grant amount:\15730000 ( Direct Cost: \12100000 、 Indirect Cost:\3630000 )

    We developed artificial DNAs whose function could be controlled by triplex formation. First we developed artificial genes incorporating pseudouracil and pseudoisocytosine which had hydrogen bond donor in their minor groove sides. The modified DNAs can be transcribed by T7-RNA polymerase and the transcrption was inhibited by the addition of triplex forming oligonucleotides incorporating artificial bases which can form hydrogen bond with pseudouracil or pseudoisocytosine. We also developed fluorescent DNAs having aromatic groups in their minor groove. The spectroscopic analyses revealed that the fluorescence of the DNAs can be enhanced by addition of triplex forming oligonucleotides.

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  • DNA-タンパク質相互作用の光制御を利用した遺伝子回路への光分子スイッチの導入

    Grant number:26119705  2014.4 - 2016.3

    日本学術振興会  科学研究費助成事業  新学術領域研究(研究領域提案型)

    清尾 康志

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    Grant amount:\13260000 ( Direct Cost: \10200000 、 Indirect Cost:\3060000 )

    新規ケージドヌクレオシドとして、1-(2-ニトロベンジル)-2'-デオキシシュードウリジンを設計し、それを含むDNAの化学合成とその三リン酸体の合成とT7-RNAポリメラーゼ反応への適用を検討した。まず、上記ヌクレオシドを2'-デオキシシュードウリジンから合成し、ホスホロアミダイトへと誘導した後、DNA自動合成機を用いてDNAを合成した。
    合成したDNAと相補鎖DNAからなる光ケージされたDNA二重鎖を用いてT7-RNAポリメラーゼによる転写反応を行った。その結果、光ケージされたDNA二重鎖と2-ニトロベンジル基を光で除去したDNAを比較すると、後者の方がより効率的に転写されることが分かった。これにより、光照射により転写効率を制御することのできる人工DNAを開発することができた。
    またこれらの結果からDNAのメジャーグルーブ側につきだした芳香環が効率的にDNA結合タンパク質と相互作用する可能性が示唆されたため核酸塩基の7位に芳香環を導入した誘導体を種々合成し、その性質を調べたところベンゾフラン-2-イル基を導入した誘導体が蛍光特性を有し、かつその蛍光がDNA結合タンパク質の結合によりOn-offされるあらたな知見も見出した。また上記ヌクレオシドを三リン酸体への変換し、DNA鎖へのKlenowフラグメントによる取り込み反応を検討したところ、合成したヌクレオシド三リン酸はチミジン三リン酸の替わりにDNA鎖に組み込まれることが分かった。上記ヌクレオシドはチミジン三リン酸の代替基質として、アデニンの相補的位置に取り込まれる事もわかった。
    以上の結果から、今回合成した1-(2-ニトロベンジル)-2'-デオキシシュードウリジンとその三リン酸はDNA合成酵素によりDNA鎖に取り込むことができ、かつT7-RNAポリメラーゼの転写効率を制御する新規光ケージドヌクレオシドであることが分かった。

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  • New miRNA detecting system utilizing fluorescent DNA triplexes and rolling circle amplification

    Grant number:25620126  2013.4 - 2015.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Exploratory Research

    SEIO KOHJI

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    Grant amount:\4160000 ( Direct Cost: \3200000 、 Indirect Cost:\960000 )

    We planed to develop new microRNA detection techniques using fluorescent oligonucleotides and rolling circle amplification. As the fluorescent nucleosides developed 5-(3-methylbenzofuran-2-yl)deoxyuridine (dUMBF), the dUMBF derivatives incorporating various substituents on its benzofuran ring, and 7-deazaguanine incorporating benzofuranyl group at the 7 position. The fluorescent properties of these nucleosides and oligonucleotides incorporating them were studied.

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  • Development of miRNA detection techniques using artificial nucleic acids capable of short RNA selective ginding

    Grant number:23350077  2011.11 - 2014.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    SEIO Kohji

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    Grant amount:\11570000 ( Direct Cost: \8900000 、 Indirect Cost:\2670000 )

    In this project, we developed new techniques for miRNA detection by using organic chemistry and nucleic acid detection platforms. We tried to improve the properties of an anrtificial nucleic acid, dAChcmp, by the chemical modificaton. We also evaluated the usefulness of the new artificial nucleic as the primers for RT-PCR. We also developed new fluorescent nucleic acids as the fluorescent probes for miRNA detection. Finally, we tried to apply these new artificial nucleic acids for miRNA detection technoques such as DNA microarray.

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  • Development of T7 promoter controlled by DNA triplex formation

    Grant number:23655154  2011

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Exploratory Research

    SEIO Kohji

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    Grant amount:\3900000 ( Direct Cost: \3000000 、 Indirect Cost:\900000 )

    We introduce a pyrimidopyrimidoindole nucleobase(PPI) and pseudouridine as the analogs of cytosine and thymidine, respectively, in T7 promoter sequence. The artificial DNA was subjected to the transcription by usint T7-RNA polymerase. As the results, it was proved that the modified T7 promoter possessed the ability to promote transcription by T7-RNA polymerase. Moreover, it was also proved that the transctiption was inhibited by the addition of triplex forming oligonucleotide capable of recognizing the modified promoter sequence

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  • Detection of miRNAs using artificial oligonucleotide probes capable of chain length discrimination

    Grant number:20350074  2008 - 2010

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    SEIO Kohji

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    Grant amount:\19630000 ( Direct Cost: \15100000 、 Indirect Cost:\4530000 )

    Artificial oligonucleoptide probes were developed for the detection of mature miRNA in living cells. The new nucleic acids derivatives such as the oligonucleotide probes having short RNA selectivity, the nucleic acid analogs capable of precise base recognition and the fluorescent nucleic acids applicable for the monitoring of the hybridization events were developed. These artificial nucleic acids are useful for the miRNA detection.

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  • Large Scaled Fast Aqueous Computing with Light Responsive DNA upon Micro Fluidic Devices

    Grant number:17200022  2005 - 2006

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (A)

    YAMAMURA Masayuki, SEIO Koji, FUJII Teruo, FUJIMOTO Kenzo

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    Grant amount:\49530000 ( Direct Cost: \38100000 、 Indirect Cost:\11430000 )

    Early explosion of DNA computing to solve combinatorial problems is now shrinking by three hardness ; (1) code set design, (2) scalability and (3) speed and reliability. This project proposes an implementation of Aqueous memory molecules by using light responsive modification of DNAs and show a series of feasibility experiments. We expect to overcome three difficulties since Aqueous computing is code design free (1), DNA sequence provides arbitrary size of address space (2), and light responsive reaction is fast and reliable (3).
    As a result of this project, Yamamura has examined a series of experiments of the write operation with a set of light responsive 11 DNA codes of 20 base pair long and shown a demonstration of Aqueous computing with four bits memory. Fujii has developed a set of necessary techniques to handle droplets on micro fluidic devices so that droplets can be generated and mixed on demand, i.e for arbitrary material, quantity and timing, and also realized continuous DNA-PNA hybridization reaction and gel electrophoresis analysis on a micro fluidic device. Seio has developed a synthesis method of branched DNA with TrS protecting group which can be deprotected by I2-promoted removal of the TrS group, and show high quality branched DNA can be synthesized than conventional method. Fujimoto has developed a method for photo-crosslinking molecules as a write once operation, and also developed a method for photoinduced repair of thymine dimmer as an enzyme free tool for Aqueous computing.

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  • 電気化学的モレキュラービーコンによる高速遺伝子検出法の開発

    Grant number:16651060  2004

    日本学術振興会  科学研究費助成事業  萌芽研究

    清尾 康志

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    Grant amount:\3600000 ( Direct Cost: \3600000 )

    本起案研究ではこれらの問題点を解決すべく、チップに固定化することなく溶液の状態で、高精度に遺伝子の検出が可能な新しい電気化学リガンドの開発を提案して、その実現に向けた基盤研究を実施した。本起案研究で提唱した「電気化学的モレキュラービーコン」は、従来の蛍光化学的モレキュラービーコンと同様シグナルのON/OFF機能を有した電気化学的分子デバイスであり、従来、精巧な微小電極やチップ技術、高価な装置が必要であった電気化学的遺伝子検出を、安価かつ容易に行えるための基盤技術の提供を目指す。
    本年の研究ではフェロセンとイオノフォアとの組み合わせによる機能性超分子のデザインと、その合成を行い、イオノフォア構造をバックボーンに組み込んだチミジン二量体ユニットの合成を以下の要領で達成した。
    チミジンの5'水酸基をジメトキシトリチル基で保護し、3'水酸基のホルミルメチル化の条件を種々検討した。その結果、一旦3'水酸基をアリル化し、次いで、四酸化オスミウムによるジオール化、過ヨウ素酸酸化を経ることで目的とするホルミルメチル化を効率よく行うことができた。また同様の工程を用いて、3'水酸基をTBDMS基で保護した、5'ホルミルメチルチミジンも効率よく合成することができた。その後、このふたつのアルデヒド化合物を3,6-ジオキサオクテン-1,8-ジアミンと還元的アミノ化を行い、チミジン二量体を合成することができた。ついで、TBDMS基の除去とアミノ基の保護、水酸基のホスフィチル化を行い、目的とするチミジン二量体ユニットを合成した。また、これを用いたオリゴDNAの合成も行った。
    以上、本研究を通してイオノフォア構造をバックボーンに組み込んだDNA合成の最大の鍵となる二量体ユニットの合成法を確立することができた。今後は今回確立した合成法を用いて、種々のオリゴDNAの合成とフェロセン残基の導入を行い、そのハイブリダイゼーション特性の評価と電気化学特性の評価を行う。

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  • ゲノム修復型遺伝子治療を指向した、機能性DNAドラッグのデザインと創製

    Grant number:15012218  2003

    日本学術振興会  科学研究費助成事業  特定領域研究

    清尾 康志

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    Grant amount:\3500000 ( Direct Cost: \3500000 )

    オリゴDNAを用いた遺伝子改変は、新しい遺伝子治療や遺伝子操作の技術として、注目されている。しかし、現段階では、その効率が非常に低いため、実用化にはいたっていない。
    本起案研究では、オリゴDNAを用いた遺伝子修復のなかでも、生体内のミスマッチ修復機構を利用した遺伝子修復に着目し、この二本鎖DNAに対する優れたストランドインベージョン能と、強力なミスマッチ塩基対形成能を有する人工DNAの創製を計画した。具体的には、高いインベージョン能を有することが期待される新規ペプチド核酸(PNA)のドラッグデザインと、起案者がすでに報告した、高いミスマッチ塩基対を有するN-アルコキシカルボニルシトシン(Roc-dC)とその誘導体の開発を行う。
    これまでに起案者が独自に開発したアルコキシカルボニルシトシン(Roc-dC)のミスマッチ塩基対形成能を高めるべく、そのコンホメーションを環状構造でロックした新規ヌクレオベースHPPのデザインと合成を行った。
    新規ヌクレオベースHPPを化学的にDNA中に導入し、そのワトソンクリック塩基対形成能、およびミスマッチ塩基対形成能をUV-融解曲線を用いて評価した。その結果、HPPが予想通り、高いワトソンクリック塩基対形成能とともに、強力なミスマッチ塩基対形成能を有していることが分った。HPPとAとのミスマッチ塩基対を含む二本鎖DNA30量体を化学合成し、ミスマッチ結合タンパクである高度好熱菌由来MutSとの結合実験を行った。その結果HPPは天然型A-Cミスマッチ塩基対と同等の効率でMutSに認識されることが分った。合成したHPPの分光学的性質を詳細に検討したところ、HPPは比較的強い蛍光発光を示すことがわかった。またその蛍光発光は二本鎖DNA中でグアニンと対合すると消失し、アデニンと対合すると発光することが分った。

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  • EXPLORATION OF ULTIMATE NEW SYNTHETIC METHOD OF DNA/RNA BY USE OF "PROTON-BLOCK APPROACH"-DIRECTED TOWARD ESTABLISHMENT OF INOVATIVE METHOD FOR THE SYNTHESIS OF NUCLEIC ACIDS WITHOUT BASE PROTECTION-

    Grant number:14208074  2002 - 2003

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (A)

    SEKINE Mitsuo, SEIO Khoji

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    Grant amount:\43940000 ( Direct Cost: \33800000 、 Indirect Cost:\10140000 )

    Previously, Ο-selective phosphorylation on polymer supports in the N-unprotected phosphoramdite method could not be carried out since the amino groups of dA and dC have high reactivity toward tervalent phosphorus(III)-type phosphitylating reagents. In this paper, we developed a new coupling strategy named 'activated phosphite method' in which the phosphitylation reaction is mediated by phosphite triester intermediates such as compound 1. In the solution-phase synthesis of TpA and TpC derivatives, the condensation by use of HOBt showed almost 100% Ο-selectivity and, they could be isolated in high yields. Subsequently, we examined the Ο-selectivity of the phosphorylation by use of various 1-hydroxybenzotriazole-and phenol-type promoters in the synthesis of dimers (ApT, CpT, and GpT) and trimers (TpApT, TpCpT, and TpGpT) on polymer supports. Application of HOBt as the promoter to the solid-phase synthesis resulted in excellent Ο-selectivity of more than 99.7%. We explained this Ο-selectivity based on the FMO interactions between the reactive intermediates and the nucleophiles such as the amino or hydroxyl groups of nucleosides. It was also found that the Ο-selectivity decreased in the condensation by use of HOBt-type promoters with an increase of the acidity of the promoter. The detailed studies on the mechanism of our present approach disclosed that, during this condensation, a phosphite benzotriazolyl ester intermediate is converted via rearrangement into the corresponding pentavalent phosphorus species which was found to be still reactive to hydroxy functions. It was estimated that contribution of this pentavalent species to the overall phosphorylation is at most 4 -10% in the condensation. Furthermore, we succeeded in the synthesis of longer oligonucleotides not only by a manual operation but also by a DNA synthesizer. The utility of our new method was demonstrated by the successful synthesis of an alkali-labile modified oligodeoxyribonucleotide having 4-N-acetyl deoxycytidine residues.

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  • ミスマッチ塩基対安定化能を有する人工DNAのデザインと開発

    Grant number:14011218  2002

    日本学術振興会  科学研究費助成事業  特定領域研究

    清尾 康志

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    Grant amount:\3900000 ( Direct Cost: \3900000 )

    オリゴヌクレオチドを用いた遺伝子修復技術はゲノムを直接書き換える遺伝子操作技術として、基礎研究や臨床での応用が期待されている。本研究ではこの遺伝子修復技術のための新素材を人工核酸のデザインと有機合成の手法を用い開発することを検討した。具体的にはミスマッチ修復酵素MutS-DNA複合体の3次元構造モデルからヒントを得た、アデニン塩基とreverse wobble型ジオメトリーでしかも非常に安定な塩基対を形成しうる人工シトシン塩基をデザインしその合成とオリゴDNAへの導入を行った。また合成した人工オリゴDNAについてはその二重鎖形成能や塩基識別能などを評価した。その結果、予想通り、今回合成した環状シトシン誘導体は、グアニン、アデニンの双方と安定な塩基対を形成することが分った。特に、アデニンとのミスマッチ塩基対については、天然型のシトシンに比べ10度以上も高いTm値を示し、そのミスマッチが著しく安定化されていることが分った。また、その塩基対構造がreverse wobble型である可能性についても示唆された。
    おどろいたことに、合成した環状シトシンは蛍光を有することが分り、この化合物が遺伝子診断やSNPs解析などのゲノムテクノロジーの分野でも興味深い特性を示すことがわかった。
    現在、遺伝子修復系のたんぱく質などと相互作用の解析などを行うための準備を検討しており、最終的には優れた遺伝子修復能を有する人工核酸新素材と開発を目指す。
    また予想外に得られたこの化合物の蛍光特性も引き続き検討を加え、遺伝子診断の分野への展開も検討する予定である。

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  • 塩基配列を精密に認識するインテリジェント核酸プローブのデザインと開発

    Grant number:13202021  2001

    日本学術振興会  科学研究費助成事業  特定領域研究(C)

    清尾 康志

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    Grant amount:\4600000 ( Direct Cost: \4600000 )

    「相補的な配列とは強固にハイブリダイズし、非相補的配列はこれを積極的に拒絶する」知的な新規メカニズムにより核酸プローブの塩基配列認識能を向上させる。具体的には、塩基対形成に際してダイナミックに構造変化するカルバモイル化核酸塩基をデザインした。シトシンへの応用から検討を開始し、2'-デオキシシチジンのカルバモイル化、オリゴDNAへの導入とハイブリダイゼーション特性を検討する。その後、順次アデニン塩基、グアニン塩基へ展開する。最終的には精密な塩基配列識別能を持った「インテリジェントプローブ」を創製し、ゲノム解析やゲノム機能解析技術のクオリティー向上を目指す。
    2001年度の計画 種々のN^4-カルバモイルシトシンとそれを含むオリゴデオキシヌクレオチドを合成し、相補的DNA及びミスマッチDNAとの二重鎖形成能を測定し、N^4-カルバモイルシトシンの相補鎖識別能を評価する。得られた知見を元に、更に分子デザインを行い、二重鎖形成能および相補鎖識別能の向上をはかる。
    2001年度の成果 種々のカルバモイルシチジン誘導体を合成し、そのコンホメーション特性を^1H-NMRスペクトルにより解析した。その結果カルバモイルシトシンが塩基対形成に伴いダイナミックに構造変化することが判った。次に合成したカルバモイルシチジンを合成DNA中に組み込み、その二重鎖形成能とミスマッチ識別能を調べた。当初の予想に反しカルバモイルシトシン誘導体はグアニンだけでなく、アデニンとも安定な塩基対を形成することが判った。この原因について計算化学的手法により解析すると、カルバモイルシトシンは通常のシトシンと比較し、イミノ型構造に互変異性しやすいことが判った。またカルバモイルシトシンの構造類縁体であるアルコキシカルボニルシトシンの塩基対形成能から、カルバモイルシトシンはアデニンと非ワトソンクリック型塩基対を形成する可能性も示唆された。

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  • 核酸の新規化学合成法の開発とその応用

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    Grant type:Competitive

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  • Developping new approaches toward the chamical synthesis of DNA and RNA.

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    Grant type:Competitive

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