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Issue 42, 2016
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Synthesis of α,ω-heterotelechelic PVP for bioconjugation, via a one-pot orthogonal end-group modification procedure

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Abstract

A simple one pot orthogonal procedure for synthesizing α-aldehyde, ω-thiol heterotelechelic poly(N-vinylpyrrolidone) (PVP) is introduced. Firstly we designed a xanthate chain transfer agent with an acetal protected aldehyde functionality in the leaving group, then we synthesized α-acetal ω-xanthate end-functional PVP, via a RAFT-mediated polymerization. The end-groups were modified via a facile, modular protocol, by first aminolysing the ω-xanthate end-groups to form thiols, using an excess of a primary amine, and subsequently acidifying the reaction medium to simultaneously convert excess primary amine to its (non-interfering) quaternary ammonium salt form, as well as effect the acid-catalysed deprotection of the acetal into an aldehyde functionality, to access the α-aldehyde, ω-thiol-PVP. Finally, we demonstrated the utility of these end-groups by performing conjugations with model small molecules. This study establishes a facile procedure for accessing different and bio-relevant end-functional groups with a biocompatible vinyl polymer, suitable for making drug delivery vehicles.

Graphical abstract: Synthesis of α,ω-heterotelechelic PVP for bioconjugation, via a one-pot orthogonal end-group modification procedure

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Publication details

The article was received on 25 Jul 2016, accepted on 27 Aug 2016 and first published on 29 Aug 2016


Article type: Paper
DOI: 10.1039/C6PY01296E
Citation: Polym. Chem., 2016,7, 6450-6456
  • Open access: Creative Commons BY-NC license
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    Synthesis of α,ω-heterotelechelic PVP for bioconjugation, via a one-pot orthogonal end-group modification procedure

    Paul. W. Reader, R. Pfukwa, S. Jokonya, G. E. Arnott and B. Klumperman, Polym. Chem., 2016, 7, 6450
    DOI: 10.1039/C6PY01296E

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