Issue 35, 2009
From the journal:

Chemical Communications

Phosphine-mediated one-pot thiol–ene “click” approach to polymer–protein conjugates†

Mathew W. Jones,a   Giuseppe Mantovani,b   Sinead M. Ryan,c   Xuexuan Wang,c   David J. Braydenc  and  David M. Haddleton*a  

* Corresponding authors

a Department of Chemistry, University of Warwick, Coventry, UK
E-mail: D.M.Haddleton@warwick.ac.uk
Fax: +44 (0)24 7652 4112
Tel: +44 (0)24 7652 3256

b School of Pharmacy, University of Nottingham, Nottingham, UK

c UCD School of Agriculture, Food Science and Veterinary Medicine and UCD Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland

Abstract

We employ water-soluble organic phosphines as key reagents in a one-pot synthetic protocol where a (poly)peptide disulfide bridge is first reduced followed by subsequent reaction of the two thiols in situ with poly(monomethoxy ethylene glycol)(meth)acrylates (p(mPEG)(M)A); we use salmon calcitonin (sCT) as a disulfide bridge-containing peptide, which contains a disulfide bridge—Cys1–Cys7—that can be reduced to give two sulfhydryl units available for thiol functionalisation; bioactivity is retained.

Graphical abstract: Phosphine-mediated one-pot thiol–ene “click” approach to polymer–protein conjugates

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Article information

DOI
https://doi.org/10.1039/B906865A
Article type
Communication
Submitted
06 Apr 2009
Accepted
30 Jun 2009
First published
21 Jul 2009

Chem. Commun., 2009, 5272-5274

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Phosphine-mediated one-pot thiol–ene “click” approach to polymer–protein conjugates

M. W. Jones, G. Mantovani, S. M. Ryan, X. Wang, D. J. Brayden and D. M. Haddleton, Chem. Commun., 2009, 5272 DOI: 10.1039/B906865A

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