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Cysteine‐Containing Polyisocyanides as Versatile Nanoplatforms for Chromophoric and Bioscaffolding
Author(s) -
Le Gac Stéphane,
Schwartz Erik,
Koepf Matthieu,
Cornelissen Jeroen J. L. M.,
Rowan Alan E.,
Nolte Roeland J. M.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200903502
Subject(s) - maleimide , thioester , chemistry , cysteine , iodoacetamide , biotinylation , streptavidin , polymer , chromophore , pyrene , combinatorial chemistry , polymer chemistry , photochemistry , organic chemistry , biotin , biochemistry , enzyme
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 4 1 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.