Recognition of quaternary ammonium salts with tetrapeptides containing α-aminoisobutyric acid as a conformational constraint
Yanagihara, Ryoji; Katoh, Masaki; Hanyuu, Masayuki; Miyazawa, Toshifumi; Yamada, Takashi; Yanagihara Ryoji; Department of Chemistry, Faculty of Science, Konan University; Katoh Masaki; Department of Chemistry, Faculty of Science, Konan University; Hanyuu Masayuki; Department of Chemistry, Faculty of Science, Konan University; Miyazawa Toshifumi; Department of Chemistry, Faculty of Science, Konan University; Yamada Takashi; Department of Chemistry, Faculty of Science, Konan University
Журнал:
Journal of the Chemical Society, Perkin Transactions 2
Дата:
2000
Аннотация:
Tetrapeptides Trp-Aib-Gly-Leu-NH-Ar (Aib: α-aminoisobutyric acid, 2-amino-2-methylpropanoic acid, Arâ =â 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<sup>+</sup>â CH3 groups of the guests were close to the aromatic moieties of the host in the complex. The charge in cation guests, the Ï -basicity of the host, and the turn conformation of the peptides were important factors for the complexation.
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