Water soluble azido polyisocyanopeptides as functional β-sheet mimics

Authors

  • Erik Schwartz,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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  • Matthieu Koepf,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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  • Heather J. Kitto,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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  • Mónica Espelt,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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  • Vicent J. Nebot-Carda,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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  • Rene De Gelder,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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  • Roeland J. M. Nolte,

    Corresponding author
    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
    • Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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  • Jeroen J. L. M. Cornelissen,

    Corresponding author
    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
    • Laboratory for Biomolecular Nanotechnology, MESA+ Institute, University of Twente, Enschede, The Netherlands
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  • Alan E. Rowan

    Corresponding author
    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
    • Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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Abstract

The design and synthesis of functional biomimetic water soluble polymers with a defined secondary structure has been developed using β-sheet polyisocyanopeptide scaffolds. Water soluble isocyanopolymers were prepared by random copolymerisation of the azido functionalized isocyanopeptides with nonfunctionalised methyl ester isocyanides derived from alanine. Upon saponification of the latter function a rigid rod water soluble polymer was obtained with an accessible azide for postfunctionalization. The potential of these biomimetic polymers was successfully demonstrated by using the click chemistry reaction of these polymers with an acetylene functionalised rhodamine dye. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 4150–4164, 2009

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