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