Cysteine-Containing Polyisocyanides as Versatile Nanoplatforms for Chromophoric and Bioscaffolding

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Gac, Stephane Le and Schwartz, Erik and Koepf, Matthieu and Cornelissen, Jeroen J.L.M. and Rowan, Alan E. and Nolte, Roeland J.M. (2010) Cysteine-Containing Polyisocyanides as Versatile Nanoplatforms for Chromophoric and Bioscaffolding. Chemistry: a European Journal, 16 (21). pp. 6176-6186. ISSN 0947-6539

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Abstract:The straightforward syntheses of polyisocyanides containing the alanine–cysteine motif in their side chains have been achieved. Detailed characterization of the polymers revealed a well-defined and highly stable helical conformation of the polyimine backbone responsible for the formation of rodlike structures of over one hundred nanometers. The 41 helix is further stabilized by β-sheet-like interactions between the peptide arms. As a result, the cysteine sulfur atoms are regularly aligned along the polymer axis, which provides a unique platform for the scaffolding of various entities by using versatile click-chemistry postmodification approaches. For instance, pyrene derivatives were introduced through thio-specific reactions involving either maleimide, iodoacetamide, or thioester groups, leading to arrays of stacked chromophores with excimer-like emission. A water-soluble cysteine-rich polyisocyanide was successfully biotinylated and coupled to streptavidin.

Item Type:Article
Copyright: © 2010 WILEY-VCH Verlag
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/77540
Official URL:http://dx.doi.org/10.1002/chem.200903502
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Metis ID: 273731