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Issue 10, 2017
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Protecting group free synthesis of glycosyl thiols from reducing sugars in water; application to the production of N-glycan glycoconjugates

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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.

Graphical abstract: Protecting group free synthesis of glycosyl thiols from reducing sugars in water; application to the production of N-glycan glycoconjugates

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Supplementary files

Article information


Submitted
17 Jan 2017
Accepted
10 Feb 2017
First published
13 Feb 2017

This article is Open Access

Org. Biomol. Chem., 2017,15, 2152-2156
Article type
Communication

Protecting group free synthesis of glycosyl thiols from reducing sugars in water; application to the production of N-glycan glycoconjugates

S. R. Alexander, D. Lim, Z. Amso, M. A. Brimble and A. J. Fairbanks, Org. Biomol. Chem., 2017, 15, 2152
DOI: 10.1039/C7OB00112F

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