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Issue 1, 2011

Optimised ‘click’ synthesis of glycopolymers with mono/di- and trisaccharides

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Abstract

In this paper we investigate the optimum procedure for the post-polymerisation modification of alkyne-bearing polymer scaffolds with glycosyl azides. We first elaborate the one-pot synthesis of glycosyl azides, in aqueous solution, without the need for protecting groups and in multigram scale. Using these azides, the ligand tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) was shown to give the fastest kinetics for the ‘click’ reaction at ambient temperature, and was used to prepare homogenous oligosaccharide-modified glycopolymers. The terminal sugars of these oligosaccharides were used to introduce α-linked glucose which is typically synthetically challenging.

Graphical abstract: Optimised ‘click’ synthesis of glycopolymers with mono/di- and trisaccharides

Supplementary files

Article information


Submitted
16 Aug 2010
Accepted
10 Sep 2010
First published
04 Oct 2010

Polym. Chem., 2011,2, 107-113
Article type
Paper

Optimised ‘click’ synthesis of glycopolymers with mono/di- and trisaccharides

N. Vinson, Y. Gou, C. R. Becer, D. M. Haddleton and M. I. Gibson, Polym. Chem., 2011, 2, 107 DOI: 10.1039/C0PY00260G

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