Synthesis of [4-5,4'-5'-Bis(d-Aminovaleric Acid)]-Gramicidin S

Autor: S\={o}fuku, Sh\={o}suke, Muramatsu, Ichiro, Okada, Kazuki, Hagitani, Akira
Zdroj: Bulletin of the Chemical Society of Japan; October 1975, Vol. 48 Issue: 10 p2888-2890, 3p
Abstrakt: An analog of gramicidin S, [4-5,4'-5'’-bis(d-aminovaleric acid)]-gramicidin S, was synthesized, in which both of the two residues of d-Phe-l-Pro of gramicidin S (GS) were replaced with d-aminovaleric acid residues (dAva). The spectra of optical rotatory dispersion (ORD) and circular dichroism (CD) of this analog suggest that its conformation in solution at room temperature is a random structure by comparison with that of GS. This analog has no antimicrobial activity. The linear peptide H-(Val-Orn-Leu-dAva-)2-OH also has no activity and its ORD and CD are nearly the same as those exhibited by the random structure of the polypeptide. These results indicate the importance of the presence of d-Phe-l-Pro in GS for the maintenance of the specific conformation.
Databáze: Supplemental Index