Issue 10, 2017
From the journal:

Organic & Biomolecular Chemistry

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

S. R. Alexander,a   D. Lim, ORCID logo a   Z. Amso,bc   M. A. Brimble ORCID logo bc  and  A. J. Fairbanks ORCID logo *ad  

* Corresponding authors

a Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand
E-mail: antony.fairbanks@canterbury.ac.nz

b School of Chemical Sciences, The University of Auckland, 23 Symonds St, Auckland 1142, New Zealand

c Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, Private Bag 92019, Auckland 1142, New Zealand

d Biomolecular Interaction Centre, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand

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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Article information

DOI
https://doi.org/10.1039/C7OB00112F
Article type
Communication
Submitted
17 Jan 2017
Accepted
10 Feb 2017
First published
13 Feb 2017
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2017,15, 2152-2156

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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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