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

An electron-deficient thiyl radical, with the reactivity complementary to thiolates, for molecular catalysis of maleate isomerization in aqueous solutions.

DOI： 10.1039/d4gc06310d

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Authorship：Last author,　Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

In this study we developed a neopentyl ²¹¹At‐labeled activated ester that incorporates a triazole spacer and applied it to the synthesis of an ²¹¹At‐labeled cetuximab. The activated ester was synthesized via the nucleophilic ²¹¹At‐astatination of a neopentyl sulfonate carrying two long alkyl chains that serve as a lipid tag, which was followed by the hydrolysis of an acetal. Additionally, we developed a novel Resin‐Assisted Purification and Deprotection (RAPD) protocol involving a solid‐phase extraction of the protected ²¹¹At‐labeled compound from the mixture of the labeling reaction, hydrolysis of the acetal on the resin, and finally an elution of the ²¹¹At‐labeled activator from the resin. This method allows the synthesis of an ²¹¹At‐labeled activated ester with high purity through a simplified procedure that circumvents the need for HPLC purification. Using this ²¹¹At‐labeled activated ester, we efficiently synthesized ²¹¹At‐labeled cetuximab in 27±1 % radiochemical yield with 95 % radiochemical purity. This ²¹¹At‐activated ester demonstrated high reactivity, and enabled the completion of the reaction with the antibody within 10 min. In comparative biodistribution studies between ²¹¹At‐labeled cetuximab and the corresponding ¹²⁵I‐labeled cetuximab in normal mice, both the thyroid and stomach showed radioactivity levels that were less than 1.0 % of the injected dose.

DOI： 10.1002/cmdc.202400369

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Authorship：Last author,　Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

We report on the syntheses of NeuAc and NeuGc‐containing glycosides via the use of double carbonyl‐protected N‐acetyl sialyl donors. The 7‐O,9‐O‐carbonyl protection of an N‐acyl‐5‐N,4‐O‐carbonyl‐protected sialyl donor markedly increased the α‐selectivity during glycosylation, particularly when glycosylating the C‐8 hydroxyl group of sialic acids. The N‐acyl carbamates were selectively opened with ethanethiol under basic conditions to provide N‐acyl amines. It is noteworthy that N‐glycolyl carbamate was more reactive to nucleophiles by comparison with the N‐acetyl carbamate due to the electron‐withdrawing oxygen in the N‐acyl group and however, allowed selective opening of the carbamates without the loss of N‐glycolyl groups. To demonstrate the utility of the approach, we began by synthesizing α(2,3) and α(2,6) sialyl galactosides. Glycosylation of the hydroxy groups of galactosides at the C‐6 position with the NeuAc and NeuGc donors provided the corresponding sialyl galactoses in good yields with excellent α‐selectivity. However, glycosylation of the 2,3‐diol galactosyl acceptor selectively provided Siaα(2,2)Gal. Next, we prepared a series of α(2,8) disialosides composed of NeuAc and NeuGc. Glycosylation of NeuGc and NeuAc acceptors at the C‐8 hydroxyl group with NeuGc and NeuAc sialyl donors provided the corresponding α(2,8) disialosides, and no significant differences were detected in the reactivities of these acceptors.

DOI： 10.1002/chem.202400883

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

The synthesis of HBP is distinguished by the β-steroselective glycosylation of phosphate and ketone formation from the 2,6-lactone through the utilization of a C1 nucleophile.

DOI： 10.1039/d4ob00139g

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acsabm.3c00846

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

In the development of an efficient ¹⁸F‐labeling method for the synthesis of PET tracers, it is essential not only to improve the efficiency of [¹⁸F]fluorine incorporation into a carrier but also to minimize non‐radioactive side products from the precursor. Highly reactive sulfonate esters are promising precursors for ¹⁸F‐nucleophilic fluorination under mild conditions. However, the expected labeling efficiency from the precursor is often hampered by its competitive degradation due to coexisting bases during ¹⁸F‐fluorination. In this report, we designed a 2‐methyl‐6‐nitrobenzenesulfonate (2‐MeNs) ester as a precursor for ¹⁸F‐fluorination, in which the methyl group suppresses hydrolysis of the sulfonate ester via steric hindrance. An increase in labeling efficiency in the ¹⁸F‐labeling of a neopentyl labeling group was observed for the neopentyl 2‐MeNs ester compared with that of the 2‐nitrobenzenesulfonate ester. Ultimately, we achieved the automated synthesis of an ¹⁸F‐labeled amino acid using a neopentyl labeling group by using a 2‐MeNs ester as a precursor.

DOI： 10.1002/ajoc.202300412

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Authorship：Last author,　Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

Radiotheranostics uses radiopharmaceuticals to combine diagnostic imaging and therapeutic intervention. Radiopharmaceuticals use radiohalogens as radioisotopes due to their unique radioactive properties, but their chemical characteristics tend to vary. Due to...

DOI： 10.1039/d3ob00944k

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

The conjugation of poly(ethylene glycol) (PEG) to therapeutic proteins or nanoparticles is a widely used pharmaceutical strategy to improve their therapeutic efficacy. However, conjugation can make PEG immunogenic and induce...

DOI： 10.1039/d3tb01723k

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

A gold-complex initiated electrophilic aromatic substitution with amidomethyl 2-alknylbenzoates shortens the process to ¹⁸F-labeled polyphenol EGCG.

DOI： 10.1039/d3ob00856h

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Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

DOI： 10.1007/s10719-023-10119-6

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Other Link： https://link.springer.com/article/10.1007/s10719-023-10119-6/fulltext.html

Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acssuschemeng.2c04349

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

After ligand stimulation, many G protein–coupled receptors (GPCRs) undergo β-arrestin–dependent desensitization, during which they are internalized and either degraded or recycled to the plasma membrane. Some GPCRs are not subject to this type of desensitization because they lack the residues required to interact with β-arrestins. We identified a mechanism of redox-dependent alternative internalization (REDAI) that promotes the internalization and degradation of the purinergic P2Y6 receptor (P2Y6R). Synthetic and natural compounds containing electrophilic isothiocyanate groups covalently modified P2Y6R at Cys220, which promoted the ubiquitylation of Lys137 and receptor internalization and degradation in various mouse and human cultured cell lines. Endogenous electrophiles also promoted ligand-dependent P2Y6R internalization and degradation. P2Y6R is highly abundant in inflammatory cells and promotes the pathogenesis of colitis. Deficiency in P2Y6R protected mice against experimentally induced colitis, and mice expressing a form of P2Y6R in which Cys220 was mutated to nonmodifiable serine were more sensitive to the induction of colitis. Several other GPCRs, including A2BAR, contain cysteine and lysine residues at the appropriate positions to mediate REDAI, and isothiocyanate stimulated the internalization of A2BAR and of a form of P2Y2R with insertions of the appropriate residues. Thus, endogenous and exogenous electrophiles may limit colitis progression through cysteine modification of P2Y6R and may also mediate internalization of other GPCRs.

DOI： 10.1126/scisignal.abj0644

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Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

Abstract

Split-virus vaccine serves as a major countermeasure against influenza virus, but its effectiveness and protective action are not complete. We previously demonstrated the effect of Benifuuki, a green tea cultivar in Japan, on enhancing the split-virus vaccine–elicited immune response. However, little is known about the detail mechanisms. Here, we show that EGCG3”Me intake significantly potentiated the vaccine-elicited hemagglutination inhibition titer increase. Flow cytometry analysis revealed the increased Toll-like receptor 5 (TLR5) expression after EGCG3”Me treatment in lamina propria dendritic cells (LPDCs) and macrophages, which play crucial roles in the humoral immune system. TLR5 expression correlated with the level of interleukin-6 (IL-6)/C–C chemokine type receptor 5, which are important mediators of the humoral immunity. Taken together, In vivo and ex vivo studies showed that EGCG3”Me potentiated the split-virus vaccine–elicited immune response accompanied with the upregulation of TLR5 in intestine and splenocyte macrophages.

DOI： 10.1038/s41598-021-02346-4

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Other Link： https://www.nature.com/articles/s41598-021-02346-4

Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.jmedchem.1c01147

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Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

DOI： 10.1038/s41428-021-00513-y

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Other Link： https://www.nature.com/articles/s41428-021-00513-y

Authorship：Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/chem.202100804

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Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.202100804

Authorship：Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/slct.202100723

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Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/slct.202100723

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

DOI： 10.1016/j.nucmedbio.2020.12.008

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Publishing type：Research paper (scientific journal)   Publisher：MDPI AG  

Because Japanese cedar pollen (JCP) contains beta-1,3-d-glucan (BG), there is concern that its lingering presence in the atmosphere, especially during its scattering period, may cause false positives in the factor-G-based Limulus amebocyte lysate (LAL) assay used to test for deep mycosis (i.e., G-test). Hence, we examined whether the LAL assay would react positively with substances contained in JCP by using the G-test to measure JCP particles and extracts. BG was purified from the JCP extract on a BG-specific affinity column, and the percentage extractability was measured using three different BG-specific quantitative methods. The G-test detected 0.4 pg BG in a single JCP particle and 10 fg from a single particle in the extract. The percentage extractability of JCP-derived BG was not significantly different among the three quantitative methods. As the JCP particles should technically have been removed during serum separation, they should be less likely to be a direct false-positive factor. However, given that the LAL-assay-positive substances in the JCP extract were not distinguishable by the three BG-specific quantitative methods, we conclude that they may cause the background to rise. Therefore, in Japan false positives arising from JCP contamination should be considered when testing patients for deep mycosis.

DOI： 10.3390/ijms22042135

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

Siglecs are sialic acid (Sia)-binding immunoglobulin-like lectins; the majority of Siglecs functions as transmembrane receptors on the immune cells via Sia residues. Recently, a new Sia binding site in Siglec-7, termed site 2, where arginine (R) 67 was critical, was identified by computational modeling and biochemical analyses, relative to the primary Sia binding site, termed site 1, containing critical R124. Here, the presence of a new essential R94 residue, which is completely conserved among all identified Siglecs, was demonstrated. A mutation of R94 residue in Siglec-7 led to the disappearance of the Sia binding property, similar to a site 1 mutation (R124A). R94 is close to R67 in site 2, and site 2 mutations at either of them abolished the ligand-binding properties to both gangliosides and glycoproteins. These data suggest that, in addition to site 1, the conserved R residue among Siglecs in site 2 is another functional site.

DOI： 10.1016/j.bbrc.2020.10.023

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

DOI： 10.1016/j.jbc.2021.100477

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

The conformational analysis of oligosaccharide is a fundamental issue in glycobiology. NMR measurements of atom-selectively 13C-labeled oligosaccharides have provided valuable information concerning their conformation, which would not be possible using nonlabeled oligosaccharides. The amount of accessible information from an atom-selectively labeled molecule, however, is limited. In this work, we report on the chemical synthesis of residue-selectively 13C- and 2H-labeled oligosaccharides and their use in conformational analysis. 1H NMR measurements of such double isotope-labeled compounds can provide a great deal of information on the dihedral angles across glycosidic linkages. We demonstrated this method in the conformational analyses of some linear and branched β(1,3)-glucan oligosaccharides.

DOI： 10.1021/acs.joc.0c01939

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Language：Japanese   Publisher：(一社)日本核医学会  

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Siglec-7 is a human CD33-like siglec, and is localised predominantly on human natural killer (NK) cells and monocytes. Siglec-7 is considered to function as an immunoreceptor in a sialic acid-dependent manner. However, the underlying mechanisms linking sialic acid-binding and function remain unknown. Here, to gain new insights into the ligand-binding properties of Siglec-7, we carried out in silico analysis and site-directed mutagenesis, and found a new sialic acid-binding region (site 2 containing R67) in addition to the well-known primary ligand-binding region (site 1 containing R124). This was supported by equilibrium dialysis, STD-NMR experiments, and inhibition analysis of GD3-binding toward Siglec-7 using synthetic sialoglycoconjugates and a comprehensive set of ganglioside-based glycoconjugates. Our results suggest that the two ligand-binding sites are potentially controlled by each other due to the flexible conformation of the C-C' loop of Siglec-7.

DOI： 10.1038/s41598-020-64887-4

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

Targeting proteins that are overexpressed in cancer cells is the major strategy of molecular imaging and drug delivery systems. The 67-kDa laminin receptor (67LR), also known as oncofetal antigen, is overexpressed in several types of cancer, including melanoma, multiple myeloma, cervical cancer and bile duct carcinoma. 67LR is involved in tumour growth, tumour metastasis and drug resistance. Green tea polyphenol (-)-epigallocatechin-3-O-gallate (EGCG) directly binds to cell-surface 67LR and induces apoptosis through the protein kinase B (Akt)/endothelial nitric oxide synthase/nitric oxide/cyclic GMP (cGMP) axis. Here we report the optimum hydroxyl group for the utilization of EGCG as a novel fluorescent EGCG-mimic imaging probe based on 67LR agonist characters, including Akt activation and inhibitory effect on viable cell number in cancer cells. 67LR specific targeting is unambiguously confirmed with the use of a non-labelled EGCG competitive assay and 67LR knockdown. Importantly, this probe strongly binds to multiple myeloma cells compared with its binding to normal cells.

DOI： 10.1016/j.bbrc.2020.03.021

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

<p>Modification of a sialic acid with just carbonyl protecting groups opened the door to a chemical synthesis of polysialic acids.</p>

DOI： 10.1039/d0cc05901c

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

The core fucose, a major modification of N-glycans, is implicated in immune regulation, such as the attenuation of the antibody-dependent cell-mediated cytotoxicity of antibody drugs and the inhibition of anti-tumor responses via the promotion of PD-1 expression on T cells. Although the core fucose regulates many biological processes, no core fucose recognition molecule has been identified in mammals. Herein, we report that Dectin-1, a known anti-β-glucan lectin, recognizes the core fucose on IgG antibodies. A combination of biophysical experiments further suggested that Dectin-1 recognizes aromatic amino acids adjacent to the N-terminal asparagine at the glycosylation site as well as the core fucose. Thus, Dectin-1 appears to be the first lectin-like molecule involved in the heterovalent and specific recognition of characteristic N-glycans on antibodies.

DOI： 10.1002/anie.201911875

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/ajoc.201800726

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

DOI： 10.1246/bcsj.20190035

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

The development of new anchoring groups is important to facilitate effective co‐sensitization in dye‐sensitized solar cells (DSSCs). Herein, stable organic D–π–A dyes that contain new heterocyclic hydantoin‐based anchoring groups have been designed, synthesized, and used in DSSCs. These dye sensitizers were evaluated in terms of their absorption spectra, electrochemical properties, and performance in DSSC devices. Although only one‐third of the amount of hydantoin‐containing dyes adsorbed onto TiO₂ relative to their cyanoacrylic‐acid‐containing analogues, they exhibited effective photoexcited electron‐transfer properties. External quantum efficiencies of over 80 % was observed, which were comparable to those of the cyanoacrylic‐acid‐containing dyes. In addition, the new hydantoin‐containing dyes exhibited significant robustness, which could allow improved stability of their corresponding photovoltaic devices under harsh conditions, such as high temperature and humidity.

DOI： 10.1002/ajoc.201700542

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Authorship：Last author,　Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

Synthesis of O‐methylated glycolipids via direct stereoselective glycosidation whose sugar moieties are related to those in phenolic glycolipids (PGLs) is reported. Treatment of 2‐O‐methyl‐rhamnosyl imidates with I₂ and nBu₄NOTf resulted in their activation under low temperature and provided the α‐rhamnosides with excellent α‐selectivity. nBu₄NOTf enhanced the electorophilicity of iodine. This methodology improved the efficiency of the synthesis of both PGL‐1 and PGL‐tb1 sugars. The process involved the formation of 2‐O‐naphthylmethyl‐α‐rhamnoside and 2‐O‐methyl‐α‐fucoside. Sequential Suzuki–Miyaura coupling using synthetic glycosides, boracyclane, and aryl bromides provided glycolipids related to PGL sugars, and was accomplished with a one‐pot process. Finally, we elucidated the immunosuppressive activities of all these synthetic compounds and found that a phenyl 3‐O‐α‐rhamnosyl‐2‐O‐methyl‐α‐rhamnoside possessing a 6‐(2‐naphthyl)hexyl group exhibited the strongest inhibitory effect.

DOI： 10.1002/chem.201703684

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Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.201703684

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

DOI： 10.1093/glycob/cwx043

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Other Link： http://orcid.org/0000-0003-1919-6309

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

DOI： 10.1002/cbic.201600694

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

DOI： 10.1038/s41598-017-02162-9

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DOI： 10.1039/c6cc09504f

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/c6cc07115e

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

DOI： 10.1080/09205063.2017.1322248

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

DOI： 10.1016/j.immuni.2016.10.012

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Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

Abstract

Feglymycin is a naturally occurring, anti-HIV and antimicrobial 13-mer peptide that includes highly racemizable 3,5-dihydroxyphenylglycines (Dpgs). Here we describe the total synthesis of feglymycin based on a linear/convergent hybrid approach. Our originally developed micro-flow amide bond formation enabled highly racemizable peptide chain elongation based on a linear approach that was previously considered impossible. Our developed approach will enable the practical preparation of biologically active oligopeptides that contain highly racemizable amino acids, which are attractive drug candidates.

DOI： 10.1038/ncomms13491

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Other Link： https://www.nature.com/articles/ncomms13491

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

DOI： 10.1021/acs.langmuir.6b01635

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DOI： 10.1002/chem.201602817

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DOI： 10.1002/chem.201602044

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DOI： 10.1002/ejoc.201600392

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DOI： 10.1002/chem.201601031

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DOI： 10.1371/journal.pone.0153002

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley-VCH Verlag  

DOI： 10.1002/chem.201504277

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DOI： 10.1002/ejoc.201501190

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DOI： 10.1039/c6ra00442c

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DOI： 10.1016/j.bmcl.2015.10.068

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DOI： 10.1002/chem.201502399

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DOI： 10.1016/j.tet.2015.06.041

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DOI： 10.1002/ejoc.201500515

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DOI： 10.1002/ejoc.201500562

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DOI： 10.1002/chem.201500979

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Publishing type：Research paper (scientific journal)   Publisher：CSIRO Publishing  

An efficient, one-flow Arndt–Eistert synthesis was demonstrated. A sequence of acid chloride formation–nucleophilic acyl substitution–Wolff rearrangement–nucleophilic addition was performed in a microflow system without isolating any intermediates, which included a potentially explosive compound. The microflow system was made from simple, inexpensive, and readily available instruments and tubes. α-Aryl esters 2a and 2b were prepared in yields of 33 and 23 % (three steps) respectively.

DOI： 10.1071/ch15342

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

DOI： 10.1556/JFC-D-14-00015

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DOI： 10.1074/jbc.M114.585901

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DOI： 10.1055/s-0034-1379184

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DOI： 10.1021/co500071x

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β(1-3)-Glucans, abundant in fungi, have the potential to activate the innate immune response against various pathogens. Although part of the action is exerted through the C-type lectin-like receptor Dectin-1, details of the interaction mechanism with respect to glucan chain-length remain unclear. In this study, we investigated a set of short β(1-3)-glucans with varying degree of polymerization (DP); 3, 6, 7, 16, and laminarin (average DP; 25), analyzing the relationship between the structure and interaction with the C-type lectin-like domain (CTLD) of Dectin-1. The interaction of short β(1-3)-glucans (DP6, DP16, and laminarin) with the CTLD of Dectin-1 was systematically analyzed by (1)H-NMR titration as well as by saturation transfer difference (STD)-NMR. The domain interacted weakly with DP6, moderately with DP16 and strongly with laminarin, the latter plausibly forming oligomeric protein-laminarin complexes. To obtain structural insights of short β(1-3)-glucans, the exchange rates of hydroxy protons were analyzed by deuterium induced (13)C-NMR isotope shifts. The hydroxy proton at C4 of laminarin has slower exchange with the solvent than those of DP7 and DP16, suggesting that laminarin has a secondary structure. Diffusion ordered spectroscopy revealed that none of the short β(1-3)-glucans including laminarin forms a double or triple helix in water. Insights into the interaction of the short β(1-3)-glucans with Dectin-1 CTLD provide a basis to understand the molecular mechanisms of β-glucan recognition and cellular activation by Dectin-1.

DOI： 10.1007/s10719-013-9510-x

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

DOI： 10.3987/COM-14-12944

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Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

DOI： 10.1038/ja.2014.7

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Other Link： http://www.nature.com/articles/ja20147

Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

DOI： 10.1039/c3ra46142d

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DOI： 10.1039/c4ra04066j

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DOI： 10.1016/j.bmc.2013.07.023

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Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

Abstract

Although understanding the high-resolution spatial distribution of bioactive small molecules is indispensable for elucidating their biological or pharmacological effects, there has been no analytical technique that can easily detect the naïve molecular localization in mammalian tissues. We herein present a novel in situ label-free imaging technique for visualizing bioactive small molecules, using a polyphenol. We established a 1,5-diaminonaphthalene (1,5-DAN)-based matrix-assisted laser desorption/ionization-mass spectrometry imaging (MALDI-MSI) technique for visualizing epigallocatechin-3-O-gallate (EGCG), the major bioactive green tea polyphenol, within mammalian tissue micro-regions after oral dosing. Furthermore, the combination of this label-free MALDI-MSI method and a standard-independent metabolite identification method, an isotopic fine structure analysis using ultrahigh-resolution mass spectrometer, allows for the visualization of spatially-resolved biotransformation based on simultaneous mapping of EGCG and its phase II metabolites. Although this approach has limitations of the detection sensitivity, it will overcome the drawbacks associated with conventional molecular imaging techniques and could contribute to biological discovery.

DOI： 10.1038/srep02805

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Other Link： https://www.nature.com/articles/srep02805.pdf

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DOI： 10.1104/pp.112.211722

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DOI： 10.1002/chem.201203865

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DOI： 10.1016/j.tetlet.2012.05.111

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

DOI： 10.1016/j.bmc.2012.04.017

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DOI： 10.1055/s-0031-1290937

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

DOI： 10.1016/j.tetlet.2012.02.065

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DOI： 10.1039/c2ob26928g

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DOI： 10.1016/j.tet.2011.09.030

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DOI： 10.1074/jbc.M111.308049

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

In this report, we describe the stereoselective synthesis of a combinatorial library comprised of 16 deoxyhexasaccharides that are related to a landomycin A sugar moiety, based on an orthogonal deprotection strategy. The use of an olivosyl donor containing a benzyl ether at the C3 position and benzoyl ester at the C4 position, and the olivosyl donor, a naphthylmethyl ether, and a p‐nitrobenzylethyl or benzyl sulfonyl ester enabled the synthesis of a set of four diolivosyl units containing a hydroxyl group at the C3 or C4 position by a simple glycosylation and deprotection procedure. Using a phenylthio 2,3,6‐trideoxyglycoside, α‐selective glycosidation proceeded without anomerization of the 2,6‐dideoxy‐β‐glycosides. In addition, alkylhydroquinone and levulinoyl groups were found to be an effective set of orthogonal protecting groups for the anomeric position and a hydroxyl group. The coupling of all combinations of trisaccharide units in a β‐selective manner was accomplished by activation of the glycosyl imidate with I₂ and Et₃SiH. No cleavage of the acid‐labile 2,3,6‐trideoxyglycoside was observed under the conditions used for the reactions. Finally, all of the protected hexasaccharides were deprotected by hydrolysis of the esters, microwave (MW) assisted cleavage of the 2‐trimethylsilylethoxymethoxy (SEM) ether, and a Birch reduction.

DOI： 10.1002/asia.200900640

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Publishing type：Research paper (scientific journal)   Publisher：Oxford University Press (OUP)  

DOI： 10.1093/glycob/cwq049

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

DOI： 10.1039/c0cc01286f

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

DOI： 10.1002/asia.201000372

Web of Science

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

In this report, we describe the convergent synthesis of β(1,3) oligosaccharides containing an aminoalkyl group. The branched heptadecasaccharide and linear hexadecasaccharide acted as ligands of dectin-1 whose binding affinity was only 10-fold weaker than that of natural SPG and exhibited dectin-1 agonist activity.

DOI： 10.1039/c0cc03153d

PubMed

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/op9002455

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Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

DOI： 10.1038/ja.2009.93

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Other Link： http://www.nature.com/articles/ja200993

Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

Sweets for my sweet! Efficient synthesis of the deoxysugar part of versipelostatin (VST) was achieved by direct and stereoselective glycosidation of the reduced VST aglycon. Comparison of the synthetic and natural VST products using NMR indicate that VST has a β‐d‐digitoxose‐(1,4)‐α‐l‐oleandrose‐(1,4)‐β‐d‐digitoxose trisaccharide. A biological assay indicates that the deoxyoligosaccharide unit of the synthetic glycoside is important for biological activity.magnified image

Efficient synthesis of the deoxysugar part of versipelostatin (VST) was achieved by direct and stereoselective glycosylation of the reduced VST aglycon. Activation of 2‐deoxyglycosyl imidate with IBr under basic conditions enables α‐selective glycosylation of β‐2‐deoxylglycosides without anomerization. Comparison of the synthetic and natural VST products using NMR indicates that versipelostatin has a β‐D‐digitoxose‐(1,4)‐α‐L‐oleandrose‐(1,4)‐β‐D‐digitoxose trisaccharide. In addition, results of a biological assay indicate that the deoxyoligosaccharide unit of the synthetic glycoside was important for biological activity of the compound.

DOI： 10.1002/asia.200800448

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/jo900176e

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ja807482t

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Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.2008.1252

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

An effective hydrophilic scaffold composed of D‐trihydroxyllysine‐based oligopeptides and its application in the synthesis of the various ¹¹¹In–DTPA conjugates with mono‐ to penta‐bisphosphonate units for use as bone tracers are described. The D‐trihydroxyllysine derivative with three orthogonal protecting groups was conjugated with functional devices at the γ position and allowed oligomerization based on peptide chemistry. The radiopharmaceutical complexes of ¹¹¹In^III with selected chelators, 4 and 8, were suitable for bone imaging. These results show that D‐trihydroxyllysine 2 was an effective building block for the synthesis of multivalent ligands applicable to medical use.

DOI： 10.1002/asia.200800250

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ol802207e

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.200701276

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

DOI： 10.1016/j.bmcl.2007.02.045

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.200604031

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Gakushin Publishing Company  

DOI： 10.4052/tigg.19.183

Scopus

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Publishing type：Research paper (scientific journal)   Publisher：The Japan Institute of Heterocyclic Chemistry  

DOI： 10.3987/com-07-s(u)22

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

An efficient solution‐phase synthesis of rac‐15‐deoxy‐Δ^12,14‐PGJ₂ (15dPGJ₂) derivatives that contain variable α and ω chains based on a polymer‐assisted strategy and their neurite‐outgrowth‐promoting activity are described. The strategy for the synthesis of PGJ₂ derivatives involves the use of a vinyl iodide bearing cyclopentenone as a key intermediate, which undergoes Suzuki–Miyaura coupling and subsequent Lewis acid catalyzed aldol condensation for incorporation of the ω and α chains, respectively. For easy access to the PGJ₂ derivatives, a polymer‐supported catalyst and scavengers were adapted for use in these four diverse steps, in which workup and purification can be performed by simple filtration of the solid‐supported reagents. By using this methodology, we succeeded in the synthesis of 16 PGJ₂ derivatives with four alkyl boranes and four aldehydes. The neurite‐outgrowth‐promoting activity of the 16 synthetic compounds in PC12 cells revealed that the side‐chains play a major role in modulating their biological activity. The carboxylic acid on the α chain improved the biological activity, although it was not absolutely required. Furthermore, a PGJ₂ derivative with a phenyl moiety on the ω chain was found to exhibit an activity comparable to that of natural 15dPGJ₂.

DOI： 10.1002/asia.200600172

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2006-950283

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.200601128

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ja0613613

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

DOI： 10.1016/j.bios.2005.08.002

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

The solid‐phase synthesis of a combinatorial cross‐conjugated dienone library based on the structure of clavulones and their biological activity are reported. Clavulones are a family of marine prostanoids, and are composed of a cross‐conjugated dienone system bearing two alkyl side‐chains. The cross‐conjugated dienone system irreversibly reacted with two nucleophiles. Our strategy for the solid‐phase synthesis of the cross‐conjugated dienones involves the Sonogashira‐coupling reaction of a solid‐supported cyclopentenone 10 bearing an acetylene group, followed by aldol condensation with aldehydes. The diphenyl derivative 7 aA was prepared from the solid‐supported cyclopentenone 10 in 56 % total yield. Combinatorial synthesis of a small library using twelve halides and eight aldehydes resulted in the production of 74 desired compounds from 98 candidates, and were detected by their mass spectra. Antiproliferative effects of the crude compounds against HeLaS3 cells showed that eleven samples showed strong antitumor activity (IC₅₀&lt;0.05 μM). Further biological examination of four purified compounds by using five tumor cell lines (A549, HeLaS3, MCF7, TMF1, and P388) revealed strong cytotoxicity comparable to that of adriamycin.

DOI： 10.1002/chem.200500793

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.200503299

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

DOI： 10.1016/j.bmcl.2005.09.028

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

DOI： 10.1124/mol.106.025866

Scopus

PubMed

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Publishing type：Research paper (scientific journal)   Publisher：The Japan Institute of Heterocyclic Chemistry  

DOI： 10.3987/com-05-s(t)30

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

Scopus

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Publishing type：Research paper (scientific journal)   Publisher：Oxford University Press (OUP)  

Abstract

We describe an efficient synthesis of H type 1 and 2 trisaccharides by one-pot glycosylation involving glycosidation of glycal epoxide.

DOI： 10.1246/cl.2005.400

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ja0450298

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

We describe an efficient synthesis of 2,6‐ and 2,3‐sialyl T antigens linked to serine in a one‐pot glycosylation. We first investigated the glycosidation of thiosialosides by varying the N‐protecting group. Modification of the C‐5 amino group of β‐thiosialosides into the N‐9‐fluorenylmethoxycarbonyl, N‐2,2,2‐trichloroethoxycarbonyl (N‐Troc), and N‐trichloroacetyl derivatives enhanced the reactivity of these compounds towards glycosidation. Addition of a minimum amount of 3 Å molecular sieves was also effective in improving the yield of α‐linked sialosides. Next, we conducted one‐pot syntheses of the glycosyl amino acids by using the N‐Troc sialyl donor. The N‐Troc derivative can be converted into the N‐acetyl derivative without racemization of the amino acids. Branched‐type one‐pot glycosylation, initiated by regioselective glycosylation of the 3,6‐dihydroxy galactoside with the N‐Troc‐β‐thiophenyl sialoside, provided the protected 2,6‐sialyl T antigen in good yield. Linear‐type one‐pot glycosylation, initiated by chemoselective glycosylation of galactosyl fluoride with the N‐Troc‐β‐thiophenyl sialoside, afforded the protected 2,3‐sialyl T antigen in excellent yield. Both protected glycosyl amino acids were converted into the fully deprotected 2,6‐ and 2,3‐sialyl T antigens linked to serine in good yields.

DOI： 10.1002/chem.200400840

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

DOI： 10.1039/b413334j

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2005-865218

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

DOI： 10.1039/b507824e

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2005-863751

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Publishing type：Research paper (scientific journal)  

DOI： 10.1021/ol049100q

Web of Science

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ol036361b

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

DOI： 10.1016/j.bmcl.2003.12.026

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

DOI： 10.1016/j.tetlet.2003.12.042

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2004-817759

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2004-815413

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2004-815421

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2004-815414

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Publishing type：Research paper (scientific journal)   Publisher：The Japan Institute of Heterocyclic Chemistry  

DOI： 10.3987/com-04-s(p)31

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ol0351854

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.200250218

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

DOI： 10.1016/s0040-4039(03)00553-7

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ol020230d

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Authorship：Lead author   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ol020150+

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2002-31926

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2002-31933

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2002-19358

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2002-33537

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Publishing type：Research paper (scientific journal)   Publisher：The Japan Institute of Heterocyclic Chemistry  

DOI： 10.3987/com-02-s(m)31

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Publishing type：Research paper (scientific journal)  

DOI： 10.1023/a:1020566928295

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

DOI： 10.1016/s0040-4039(01)01944-x

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2001-18777

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-2001-15164

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

DOI： 10.1016/S0960-894X(98)00606-4

Web of Science

Scopus

PubMed

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

DOI： 10.1016/s0960-894x(98)00605-2

Web of Science

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.199715241

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-1997-807

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.199618351

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

DOI： 10.1016/0040-4039(96)00311-5

Scopus

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/anie.199316571

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Language：Japanese  

J-GLOBAL

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J-GLOBAL

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J-GLOBAL

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J-GLOBAL

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Language：Japanese   Publisher：(公社)日本栄養・食糧学会  

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Language：Japanese   Publisher：日本化学会  

CiNii Books

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J-GLOBAL

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Language：Japanese  

J-GLOBAL

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Language：Japanese  

CiNii Books

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Other Link： http://search.jamas.or.jp/link/ui/2008055986

Language：Japanese   Publishing type：Article, review, commentary, editorial, etc. (other)   Publisher：有機合成化学協会  

DOI： 10.5059/yukigoseikyokaishi.65.795

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J-GLOBAL

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Language：Japanese   Publisher：秀潤社  

CiNii Books

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Language：English   Publishing type：Research paper, summary (international conference)  

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Language：Japanese   Publisher：The Society of Synthetic Organic Chemistry, Japan  

DOI： 10.5059/yukigoseikyokaishi.60.490

CiNii Books

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J-GLOBAL

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J-GLOBAL

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J-GLOBAL

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DOI： 10.5059/yukigoseikyokaishi.56.987

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Event date： 2025.3

Language：Japanese  

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Event date： 2025.3

Language：Japanese  

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Event date： 2025.3

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Event date： 2025.3

Language：Japanese  

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Event date： 2024.9

Language：English   Presentation type：Oral presentation (general)  

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Event date： 2024.9

Language：English   Presentation type：Poster presentation  

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Event date： 2024.9

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Event date： 2024.9

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Event date： 2024.5

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Event date： 2024.3

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Event date： 2023.11

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2023.11

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Event date： 2023.11

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Event date： 2023.11

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Presentation type：Oral presentation (general)  

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Event date： 2023.8

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Event date： 2023.3

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Applicant：国立大学法人東京工業大学

Application no：特願2013-188989  Date applied：2013.9

Announcement no：特開2015-054840  Date announced：2015.3

J-GLOBAL

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Applicant：国立大学法人東京工業大学, 日本メジフィジックス株式会社

Application no：特願2013-159041  Date applied：2013.7

Announcement no：特開2015-030747  Date announced：2015.2

Patent/Registration no：特許第6170368号  Date registered：2017.7 

J-GLOBAL

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Applicant：国立大学法人東京工業大学, 積水化学工業株式会社

Application no：特願2013-008476  Date applied：2013.1

Announcement no：特開2014-139534  Date announced：2014.7

J-GLOBAL

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Applicant：国立大学法人東京工業大学, 国立大学法人 新潟大学

Application no：特願2011-553844  Date applied：2011.2

Patent/Registration no：特許第5835801号  Date registered：2015.11 

J-GLOBAL

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Applicant：国立大学法人東京工業大学, 国立大学法人九州大学

Application no：特願2010-028974  Date applied：2010.2

Announcement no：特開2011-162506  Date announced：2011.8

J-GLOBAL

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Applicant：日本メジフィジックス株式会社

Application no：特願2007-110626  Date applied：2007.4

Announcement no：特開2008-266194  Date announced：2008.11

J-GLOBAL

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Applicant：国立大学法人東京工業大学

Application no：特願2006-017671  Date applied：2006.1

Announcement no：特開2007-197362  Date announced：2007.8

Patent/Registration no：特許第4992074号  Date registered：2012.5 

J-GLOBAL

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Applicant：国立大学法人東京工業大学

Application no：特願2004-264922  Date applied：2004.9

Announcement no：特開2006-078418  Date announced：2006.3

J-GLOBAL

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Applicant：高橋 孝志

Application no：特願2003-436789  Date applied：2003.12

Announcement no：特開2005-187440  Date announced：2005.7

J-GLOBAL

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Applicant：高橋 孝志

Application no：特願2003-436790  Date applied：2003.12

Announcement no：特開2005-187441  Date announced：2005.7

J-GLOBAL

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Applicant：藤沢薬品工業株式会社

Application no：特願2003-371127  Date applied：2003.10

Announcement no：特開2005-134258  Date announced：2005.5

J-GLOBAL

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Applicant：高橋 孝志

Application no：特願2003-309716  Date applied：2003.9

Announcement no：特開2005-075794  Date announced：2005.3

J-GLOBAL

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Applicant：オリンパス株式会社, 高橋 孝志, 田中 浩士

Application no：特願2003-280113  Date applied：2003.7

Announcement no：特開2005-043317  Date announced：2005.2

J-GLOBAL

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Applicant：第一製薬株式会社

Application no：特願2003-134530  Date applied：2003.5

Announcement no：特開2004-339080  Date announced：2004.12

J-GLOBAL

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Applicant：東レ株式会社

Application no：特願2003-088409  Date applied：2003.3

Announcement no：特開2004-292386  Date announced：2004.10

J-GLOBAL

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Applicant：東京工業大学長, 藤沢薬品工業株式会社

Application no：特願2001-297782  Date applied：2001.9

Announcement no：特開2003-026698  Date announced：2003.1

J-GLOBAL

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Applicant：大日本住友製薬株式会社

Application no：特願2000-567517  Date applied：1999.8

Patent/Registration no：特許第4497340号  Date registered：2010.4 

J-GLOBAL

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Applicant：住友製薬株式会社, 住友化学工業株式会社

Application no：特願平10-235787  Date applied：1998.8

Announcement no：特開2000-063381  Date announced：2000.2

J-GLOBAL

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Applicant：大日本住友製薬株式会社, 住友化学株式会社

Application no：特願平10-225750  Date applied：1998.8

Announcement no：特開2000-053654  Date announced：2000.2

Patent/Registration no：特許第4315300号  Date registered：2009.5 

J-GLOBAL

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Applicant：住友化学株式会社

Application no：特願平10-139404  Date applied：1998.5

Announcement no：特開平11-335360  Date announced：1999.12

Patent/Registration no：特許第4244398号  Date registered：2009.1 

J-GLOBAL

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