Ligand-Controlled Stereoselective Synthesis and Biological Activity of 2-Exomethylene Pseudo-glycoconjugates: Discovery of Mincle-Selective Ligands

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  • Ikazaki, Takahiro
    Graduate School of Pharmaceutical Science, Kyushu University
  • Ishikawa, Eri
    Department of Molecular Immunology Research Institute for Microbial Diseases, Osaka University Laboratory of Molecular Immunology Immunology Frontier Research Center, Osaka University
  • Tamashima, Hiroto
    Graduate School of Pharmaceutical Science, Kyushu University
  • Akiyama, Hisako
    Juntendo Advanced Research Institute for Health Science, Juntendo University RIKEN Center for Brain Science
  • Kimuro, Yusuke
    Graduate School of Pharmaceutical Science, Kyushu University
  • Yoritate, Makoto
    Graduate School of Pharmaceutical Science, Kyushu University
  • Matoba, Hiroaki
    Graduate School of Pharmaceutical Science, Kyushu University
  • Imamura, Akihiro
    Department of Applied Bioorganic Chemistry and Institute for Glyco-core Research (iGCORE), Gifu University
  • Ishida, Hideharu
    Department of Applied Bioorganic Chemistry and Institute for Glyco-core Research (iGCORE), Gifu University
  • Yamasaki, Sho
    Department of Molecular Immunology Research Institute for Microbial Diseases, Osaka University Laboratory of Molecular Immunology Immunology Frontier Research Center, Osaka University
  • Hirai, Go
    Graduate School of Pharmaceutical Science, Kyushu University

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  • Ligand‐Controlled Stereoselective Synthesis and Biological Activity of 2‐Exomethylene Pseudo‐glycoconjugates: Discovery of Mincle‐Selective Ligands
  • Ligand-controlled Stereoselective Synthesis and Biological Activities of 2-Exomethylene Pseudo-glycoconjugates: Discovery of Mincle-Selective Ligands

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Glycoconjugate analogues in which the sp^3-hybridized C2 position of the carbohydrate structure (normally bearing a hydroxy group) is converted into a compact sp2-hybridized exomethylene group are expected to have unique biological activities. We established ligand-controlled Tsuji–Trost-type glycosylation methodology to directly prepare a variety of these 2-exomethylene pseudo-glycoconjugates, including glucosylceramide analogues, in an α- or β-selective manner. Glucocerebrosidase GBA1 cleaves these synthetic pseudo-β-glucosylceramides similarly to native glucosylceramides. The pseudo-glucosylceramides exhibit selective ligand activity towards macrophage-inducible C-type lectin (Mincle), but unlike native glucosylceramides, are inactive towards CD1d.

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