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Issue 23, 2008
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Peptide/proteinpolymer conjugates: synthetic strategies and design concepts

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This feature article provides a compilation of tools available for preparing well-defined peptide/proteinpolymer conjugates, which are defined as hybrid constructs combining (i) a defined number of peptide/protein segments with uniform chain lengths and defined monomer sequences (primary structure) with (ii) a defined number of synthetic polymer chains. The first section describes methods for post-translational, or direct, introduction of chemoselective handles onto natural or synthetic peptides/proteins. Addressed topics include the residue- and/or site-specific modification of peptides/proteins at Arg, Asp, Cys, Gln, Glu, Gly, His, Lys, Met, Phe, Ser, Thr, Trp, Tyr and Val residues and methods for producing peptides/proteins containing non-canonical amino acids by peptide synthesis and protein engineering. In the second section, methods for introducing chemoselective groups onto the side-chain or chain-end of synthetic polymers produced by radical, anionic, cationic, metathesis and ring-opening polymerization are described. The final section discusses convergent and divergent strategies for covalently assembling polymers and peptides/proteins. An overview of the use of chemoselective reactions such as Heck, Sonogashira and Suzuki coupling, Diels–Alder cycloaddition, Click chemistry, Staudinger ligation, Michael’s addition, reductive alkylation and oxime/hydrazone chemistry for the convergent synthesis of peptide/proteinpolymer conjugates is given. Divergent approaches for preparing peptide/proteinpolymer conjugates which are discussed include peptide synthesis from synthetic polymer supports, polymerization from peptide/protein macroinitiators or chain transfer agents and the polymerization of peptide side-chain monomers.

Graphical abstract: Peptide/protein–polymer conjugates: synthetic strategies and design concepts

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Publication details

The article was received on 21 Dec 2007, accepted on 06 Feb 2008 and first published on 17 Apr 2008

Article type: Feature Article
DOI: 10.1039/B719689J
Chem. Commun., 2008, 2591-2611

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    Peptide/proteinpolymer conjugates: synthetic strategies and design concepts

    M. A. Gauthier and H. Klok, Chem. Commun., 2008, 2591
    DOI: 10.1039/B719689J

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