Efficient Usage of Thiocarbonates for Both the Production and the Biofunctionalization of Polymers

Authors

  • Cyrille Boyer,

    1. Centre for Advanced Macromolecular Design (CAMD), School of Chemical Sciences and Engineering, The University of New South Wales, Sydney NSW 2052 Australia
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  • Volga Bulmus,

    Corresponding author
    1. School of Biotechnology and Biomolecular Sciences (BABS), The University of New South Wales, Sydney NSW 2052 Australia
    • School of Biotechnology and Biomolecular Sciences (BABS), The University of New South Wales, Sydney NSW 2052 Australia.
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  • Thomas P. Davis

    Corresponding author
    1. Centre for Advanced Macromolecular Design (CAMD), School of Chemical Sciences and Engineering, The University of New South Wales, Sydney NSW 2052 Australia
    • Centre for Advanced Macromolecular Design (CAMD), School of Chemical Sciences and Engineering, The University of New South Wales, Sydney NSW 2052 Australia.
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Abstract

End group modification of polymers prepared by reversible addition–fragmentation chain transfer (RAFT) polymerization was accomplished by conversion of trithiocarbonate into reactive functions able to conjugate easily with biomolecules or bioactive functionality. Polymers were prepared by RAFT, and subsequent aminolysis led to sulfhydryl-terminated polymers that reacted in situ with an excess of dithiopyridyl disulfide to yield pyridyl disulfide-terminated macromolecules or in the presence of ene to yield functional polymers. In the first route, the pyridyl disulfide end groups allowed coupling with oligonucleotide and peptide. The second approach exploited thiol–ene chemistry to couple polymers and model compounds such as carbohydrate and biotin with high yield.

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