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

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 u...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017, Vol.15 (10), p.2152-2156
Main Authors: Alexander, S R, Lim, D, Amso, Z, Brimble, M A, Fairbanks, A J
Format: Article
Language:English
Subjects:
Glycoconjugates - chemical synthesis
Glycoconjugates - chemistry
Molecular Structure
Polysaccharides - chemical synthesis
Polysaccharides - chemistry
Sugars - chemistry
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
Water - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00112f