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Issue 1, 2011
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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

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Publication details

The article was received on 16 Aug 2010, accepted on 10 Sep 2010 and first published on 04 Oct 2010


Article type: Paper
DOI: 10.1039/C0PY00260G
Citation: Polym. Chem., 2011,2, 107-113
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    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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