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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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Publication details

The article was received on 17 Jan 2017, accepted on 10 Feb 2017 and first published on 13 Feb 2017


Article type: Communication
DOI: 10.1039/C7OB00112F
Citation: Org. Biomol. Chem., 2017,15, 2152-2156
  • Open access: Creative Commons BY-NC license
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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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