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Issue 3, 2013
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Poly(azlactone)s: versatile scaffolds for tandem post-polymerisation modification and glycopolymer synthesis

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Abstract

The synthesis of polymers with latent reactivity suitable for ‘click’ type modifications in a tandem post-polymerisation modification process starting with poly(azlactone) precursors is investigated. Poly(azlactones), obtained by copper(I) mediated radical polymerisation, were functionalised in a one-pot process with amines bearing functional groups which are incompatible with controlled radical polymerisation: alkynes, alkenes, furfuryl and phenol. The reaction is quantitative and 100% atom efficient presenting an efficient route to clickable scaffolds without the need for protecting group chemistry. Additionally, the poly(azlactones) were exploited to obtain synthetic glycopolymers. The ring opening procedure introduces a 5-atom spacer between glycan and backbone, which provides improved access to carbohydrate-binding proteins with deep binding pockets, such as the cholera toxin, for anti-adhesion applications.

Graphical abstract: Poly(azlactone)s: versatile scaffolds for tandem post-polymerisation modification and glycopolymer synthesis

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Article information


Submitted
17 Sep 2012
Accepted
08 Oct 2012
First published
08 Oct 2012

Polym. Chem., 2013,4, 717-723
Article type
Paper

Poly(azlactone)s: versatile scaffolds for tandem post-polymerisation modification and glycopolymer synthesis

M. W. Jones, S. Richards, D. M. Haddleton and M. I. Gibson, Polym. Chem., 2013, 4, 717
DOI: 10.1039/C2PY20757E

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