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Issue 8, 2018
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A double-click approach to the protecting group free synthesis of glycoconjugates

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Abstract

The use of a bi-functional linker, containing an alkyne and an alkene, allows the protecting group free conjugation of reducing sugars to thiols via a double click process. Firstly the linker is attached to the sugar via one-pot glycosyl azide formation and Cu-catalysed azide–alkyne cycloaddition. Photochemical thiol–ene click reaction then allows conjugation to a range of thiols, including cysteine residues of peptides.

Graphical abstract: A double-click approach to the protecting group free synthesis of glycoconjugates

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Article information


Submitted
10 Jan 2018
Accepted
30 Jan 2018
First published
06 Feb 2018

Org. Biomol. Chem., 2018,16, 1258-1262
Article type
Communication

A double-click approach to the protecting group free synthesis of glycoconjugates

S. R. Alexander, G. M. Williams, M. A. Brimble and A. J. Fairbanks, Org. Biomol. Chem., 2018, 16, 1258
DOI: 10.1039/C8OB00072G

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