化学
糖基
烷基
糖基化
组合化学
催化作用
糖肽
偶联反应
胺气处理
电泳剂
有机化学
生物化学
抗生素
作者
Yi Wei,Quanquan Wang,Ming Joo Koh
标识
DOI:10.1002/anie.202214247
摘要
Abstract C ‐Alkyl glycosides and glycoproteins exist in natural products and are prized for their role as carbohydrate mimics in drug design. However, a practical strategy that merges glycosyl donors with readily accessible reagents, derived from abundant carboxylic acid and amine feedstocks, is yet to be conceived. Herein, we show that a nickel catalyst promotes C−C coupling between glycosyl halides and aliphatic acids or primary amines (converted into redox‐active electrophiles in one step), in the presence of Hantzsch ester and LiI (or Et 3 N) under blue LED illumination to deliver C ‐alkyl glycosides with high diastereoselectivity. Mechanistic studies support the photoinduced formation of alkyl radicals that react with a glycosyl nickel species generated in situ to facilitate cross‐coupling. Through this manifold, innate CO 2 H and NH 2 motifs embedded within amino acids and oligopeptides are selectively capped and functionalized to afford glycopeptide conjugates through late‐stage glycosylation.
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