Linkage-Editing Pseudo-Glycans: A Reductive α-Fluorovinyl-C-Glycosylation Strategy to Create Glycan Analogs with Altered Biological Activities

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  • Moriyama, Takahiro
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Yoritate, Makoto
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Kato, Naoki
    Faculty of Agriculture, Setsunan University RIKEN Center for Sustainable Resource Science
  • Saika, Azusa
    Microbial Research Center for Health and Medicine, National Institutes of Biomedical Innovation, Health and Nutrition Institute of Molecular and Cell Biology, Agency for Science, Technology and Research
  • Kusuhara, Wakana
    Research Institute for Microbial Diseases, Osaka University Immunology Frontier Research Center, Osaka University
  • Ono, Shunsuke
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Nagatake, Takahiro
    Microbial Research Center for Health and Medicine, National Institutes of Biomedical Innovation, Health and Nutrition Department of Life Sciences, School of Agriculture, Meiji University
  • Koshino, Hiroyuki
    RIKEN Center for Sustainable Resource Science
  • Kiya, Noriaki
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Moritsuka, Natsuho
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Tanabe, Riko
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Hidaka, Yu
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Usui, Kazuteru
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Chiba, Suzuka
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Kudo, Noyuri
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Nakahashi, Rintaro
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Igawa, Kazunobu
    Institute for Materials Chemistry and Engineering, IRCCS, Kyushu University
  • Matoba, Hiroaki
    Graduate School of Pharmaceutical Sciences, Kyushu University
  • Tomooka, Katsuhiko
    Institute for Materials Chemistry and Engineering, IRCCS
  • Ishikawa, Eri
    Research Institute for Microbial Diseases, Osaka University Immunology Frontier Research Center, Osaka University
  • Takahashi, Shunji
    RIKEN Center for Sustainable Resource Science
  • Kunisawa, Jun
    Microbial Research Center for Health and Medicine, National Institutes of Biomedical Innovation, Health and Nutrition
  • Yamasaki, Sho
    Research Institute for Microbial Diseases, Osaka University Immunology Frontier Research Center, Osaka University
  • Hirai, Go
    Graduate School of Pharmaceutical Sciences, Kyushu University RIKEN Center for Sustainable Resource Science

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  • Linkage-Editing Pseudo-Glycans: A Reductive α-Fluorovinyl-<i>C</i>-Glycosylation Strategy to Create Glycan Analogs with Altered Biological Activities

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The acetal (O-glycoside) bonds of glycans and glycoconjugates are chemically and biologically vulnerable, and therefore C-glycosides are of interest as more stable analogs. We hypothesized that, if the O-glycoside linkage plays a vital role in glycan function, the biological activities of C-glycoside analogs would vary depending on their substituents. Based on this idea, we adopted a “linkage-editing strategy” for the creation of glycan analogs (pseudo-glycans). We designed three types of pseudo-glycans with CH2 and CHF linkages, which resemble the O-glycoside linkage in terms of bond lengths, angles, and bulkiness, and synthesized them efficiently by means of fluorovinyl C-glycosylation and selective hydrogenation reactions. Application of this strategy to isomaltose (IM), an inducer of amylase expression, and α-GalCer, which activates iNKT cells, resulted in the discovery of CH2-IM, which shows increased amylase production ability, and CHF-α-GalCer, which shows activity opposite that of native α-GalCer, serving as an antagonist of iNKT cells.

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