In:
Angewandte Chemie, Wiley, Vol. 135, No. 22 ( 2023-05-22)
Abstract:
Glycoconjugate analogues in which the sp 3 ‐hybridized C2 position of the carbohydrate structure (normally bearing a hydroxy group) is converted into a compact sp 2 ‐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.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v135.22
DOI:
10.1002/ange.202302569
Language:
English
Publisher:
Wiley
Publication Date:
2023
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514305-6
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505872-7
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1479266-7
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