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Cyclic Peptide–Polymer Complexes and Their Self‐Assembly
Author(s) -
Bélanger Dominique,
Tong Xia,
Soumaré Sadia,
Dory Yves L.,
Zhao Yue
Publication year - 2009
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.200802337
Subject(s) - hydrogen bond , stacking , polymer , supramolecular chemistry , self assembly , cyclic peptide , peptide , amide , vinyl alcohol , polymer chemistry , chemistry , aqueous solution , non covalent interactions , side chain , carboxylic acid , materials science , combinatorial chemistry , organic chemistry , molecule , biochemistry
Pepped up polymers : The synthesis and properties of novel chiral cyclic peptides designed to complex with suitable polymers through hydrogen bonding are described. A substituted cyclic peptide self‐assembles into supramolecular nanotubes and develops noncovalent interactions with poly(vinyl alcohol) (PVA) by means of its carboxyl side chains.The efficient synthesis of novel chiral cyclic peptides cyclo[NHCHX‐CHCHCH 2 CO(NHCH 2 CHCHCH 2 CO) 2 ] designed to develop hydrogen‐bonding interactions with suitable polymers is described. Complexation of a carboxylic acid derivatized cyclic peptide 2 (X=CH 2 OCOCH 2 CH 2 CO 2 H) capable of self‐assembling as “endless” tubes, with poly(vinyl alcohol) (PVA) led to a vast weak‐interaction network, in which the cyclopeptide developed extensive hydrogen‐bonding interactions with the hydroxyl groups of PVA through not only the carboxylic acid, but also its ester carbonyl and amide groups. In aqueous solution, the peptide/PVA complexes self‐assemble into long‐grain ricelike aggregates compatible with the stacking of cyclic peptides through intercycle hydrogen bonds. Upon casting on silicon wafer, the anisotropic aggregates can coalesce to form filaments tens of micrometers long. The study demonstrates that complexing functionalized cyclic peptides with polymers through hydrogen bonding is a useful approach for using polymers to mediate the self‐assembly and self‐organization of cyclic peptides.