Recognition of quaternary ammonium salts with tetrapeptides containing α-aminoisobutyric acid as a conformational constraint

Autor: Yanagihara, Ryoji, Katoh, Masaki, Hanyuu, Masayuki, Miyazawa, Toshifumi, Yamada, Takashi
Zdroj: Journal of the Chemical Society, Perkin Transactions 2; March 1, 2000, Vol. 2000 Issue: 3 p551-556, 6p
Abstrakt: Tetrapeptides Trp-Aib-Gly-Leu-NH-Ar (Aib: α-aminoisobutyric acid, 2-amino-2-methylpropanoic acid, Ar = phenyl or 3,5-dimethylphenyl) were synthesized. The peptides bound quaternary ammonium salts as guests in CDCl3. For every guest, the binding constant K of the peptide host which has a 3,5-dimethylphenyl group was larger than that of the host which has a phenyl group. ROESY analysis of the complex revealed that the N+–CH3 groups of the guests were close to the aromatic moieties of the host in the complex. The charge in cation guests, the π-basicity of the host, and the turn conformation of the peptides were important factors for the complexation.
Databáze: Supplemental Index