Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation†,10.1039/C6OB01069E

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation†

Stewart R. Alexander

Organic & Biomolecular Chemistry Pub Date : 06/14/2016 00:00:00 , DOI:10.1039/C6OB01069E

Abstract

Unprotected carbohydrates can be directly converted into cyanomethyl thioglycosides in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution in the presence of triethylamine. Reaction with methoxide provides 2-imino-2-methoxyethyl (IME) thioglycosides, which may be used directly for the glycosylation of surface protein lysine residues.