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Issue 5, 2014
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Disulfide bridge based conjugation of peptides to RAFT polymers

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Abstract

The reaction between bisulfones and the disulfide bridge of peptides or proteins allows the efficient bioconjugation without the loss of biological activity, which is often based on the three-dimensional structure of the biomolecule. This concept has been successfully applied using low molecular weight model compounds and PEG. In this article, RAFT polymers were postmodified to introduce bisulfone end-functionalities. This general approach has been tested here using poly(N-vinylpyrrolidone) PVP, which was prepared via RAFT polymerization. RAFT endgroup removal, followed by the reaction with divinyl sulfone and the bisulfone linker led to a disulfide reactive polymer. NMR studies, MALDI-TOF MSMS and SDS-PAGE confirm the successful reaction between somatostatin, a cyclic hormone peptide and the end-functionalized PVP. The RAFT process as a source to potential polymers widens the scope of this bioconjugation technique to a large array of potential structures.

Graphical abstract: Disulfide bridge based conjugation of peptides to RAFT polymers

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Publication details

The article was received on 10 Oct 2013, accepted on 25 Nov 2013 and first published on 26 Nov 2013


Article type: Paper
DOI: 10.1039/C3PY01412F
Polym. Chem., 2014,5, 1772-1781

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    Disulfide bridge based conjugation of peptides to RAFT polymers

    L. McDowall and M. H. Stenzel, Polym. Chem., 2014, 5, 1772
    DOI: 10.1039/C3PY01412F

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