Protecting group free synthesis of glycosyl thiols from reducing sugars in water; application to the production of N-glycan glycoconjugates. Issue 10 (17th February 2017)

• Record Type: Journal Article
• Authors: Alexander, S. R.; Lim, D.; Amso, Z.; Brimble, M. A.; Fairbanks, A. J.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 10(2017)
• Page Start: 2152
• Page End: 2156
• Publication Date: 2017-02-17
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00112f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Un-protected 2-acetamido terminated reducing sugars may be converted into the corresponding glycosyl thiols in water, and conjugated to peptides using the thiol–ene click reaction without recourse to any protecting groups. Abstract : Glycosyl thiols may be accessed from the corresponding reducing sugars in water without recourse to any sugar projecting groups by way of a DMC mediated reaction with thioacetic acid in the presence of base, and hydrolysis of the anomeric thioacetate. Glycosyl thiols produced by this method may be used to access glycoconjugates, such as glycopeptides by use of the thiol–ene click reaction.