title: Cysteine-containing polyisocyanides as versatile nanoplatforms for chromophoric and bioscaffolding.
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 4(1) helix is further stabilized by beta-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.
authors.affiliation: Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands. stephane.legac@univ-rennes1.fr
authors.forename: Stéphane
authors.initials: S
authors.lastname: Le Gac
authors.forename: Erik
authors.initials: E
authors.lastname: Schwartz
authors.forename: Matthieu
authors.initials: M
authors.lastname: Koepf
authors.forename: Jeroen J L M
authors.initials: JJ
authors.lastname: Cornelissen
authors.forename: Alan E
authors.initials: AE
authors.lastname: Rowan
authors.forename: Roeland J M
authors.initials: RJ
authors.lastname: Nolte
mesh_terms: D002942:Circular Dichroism; D003486:Cyanides / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry*; D036103:Nanotechnology; D011108:Polymers / Q000737:chemistry*; D017433:Protein Structure, Secondary; D013056:Spectrophotometry, Ultraviolet
chemical_list: D003486:Cyanides; D011108:Polymers; D003545:Cysteine