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Studies of Peptide Antibiotics. XIV. Analogs of Gramicidin S Containing D-Valine or D-Leucine in Place of D-Phenylalanine

1969; Oxford University Press; Volume: 42; Issue: 3 Linguagem: Inglês

10.1246/bcsj.42.782

1348-0634

Haruhiko Aoyagi, Tetsuo Kato, Michinori Waki, Okitoshi Abe, Reiko Okawa, Satoru Makisumi, Nobuo Izumiya,

Biopolymer Synthesis and Applications

Abstract Two analogs of gramicidin S, 4,4′-d-valine- and 4,4′-d-leucine-gramicidin S (XVI-A and XVI-B), have been synthesized and tested for the antibacterial properties. The crude product obtained after the cyclization of a linear pentapeptide active ester was composed of the protected monomer and dimer. The pure protected dimer was obtained by a column chromatography of Sephadex LH-20, and the hydrogenolysis of this product in the presence of hydrogen chloride afforded the crystalline hydrochloride of XVI-A or XVI-B. These analogs were as active as natural gramicidin S; the results indicated that the aromatic side chains of the d-phenylalanines in the molecule of gramicidin S can be replaced by the aliphatic side chains without an influence for the activity.