Issue 3, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
17 Sep 2012
Accepted
08 Oct 2012
First published
08 Oct 2012

Polym. Chem., 2013,4, 717-723

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements