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Facile synthesis of 1,4-cis-polyisoprene–polypeptide hybrids with different architectures

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Abstract

The synthesis of polypeptide hybrids by controlled/living ring-opening polymerization of N-carboxyanhydrides (NCA) using Schreiner's thiourea catalyst and amino-alcohol terminated poly(1,4-cis-isoprene)s as initiators was demonstrated for γ-benzyl-L-glutamate (BLG) and ε-tert-butyloxycarbonyl-L-lysine (BLL) NCAs. One-pot synthesis of amino-alcohol terminated macroinitiators from heterotelechelic keto/aldehyde polyisoprene by reductive amination of carbonyl(s) was presented. Selection of amines allowed to obtain mono-, di- and tri-functional macroinitiators that were used for the synthesis of polyisoprene–polypeptide hybrids of different architecture: AB, BAB, AB2, BAB2, CBABC. Due to the living character of the polymerization, the molar mass of the polypeptide blocks could be controlled by the monomer to initiator ratio (6000 < Mn < 44 000 g mol−1), while sequential monomer addition allowed the synthesis of a pentablock terpolymer: poly(BLG-b-BLL-b-isoprene-b-BLL-b-BLG).

Graphical abstract: Facile synthesis of 1,4-cis-polyisoprene–polypeptide hybrids with different architectures

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Publication details

The article was received on 14 Feb 2019, accepted on 09 Apr 2019 and first published on 09 Apr 2019


Article type: Paper
DOI: 10.1039/C9PY00241C
Citation: Polym. Chem., 2019, Advance Article

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    Facile synthesis of 1,4-cis-polyisoprene–polypeptide hybrids with different architectures

    A. V. Radchenko, J. Grange, A. Vax, F. Jean-Baptiste-dit-Dominique, R. Matmour, S. Grelier and F. Peruch, Polym. Chem., 2019, Advance Article , DOI: 10.1039/C9PY00241C

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