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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 exp...ected 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.続きを見る
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