Issue 8, 2018
From the journal:

Organic & Biomolecular Chemistry

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

S. R. Alexander,a   G. M. Williams,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

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

DOI
https://doi.org/10.1039/C8OB00072G
Article type
Communication
Submitted
10 Jan 2018
Accepted
30 Jan 2018
First published
06 Feb 2018

Org. Biomol. Chem., 2018,16, 1258-1262

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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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