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Studies of Peptide Antibiotics. XV. The Synthesis of cyclo -(L-Valyl-L-ornithyl-L-leueyl-D-phenylalanyl-L-prolyl-glycyl-glycyl)

1970; Oxford University Press; Volume: 43; Issue: 3 Linguagem: Inglês

10.1246/bcsj.43.914

1348-0634

Okitoshi Abe, Kenji Kuromizu, Michio Kondo, Nobuo Izumiya,

Antimicrobial Peptides and Activities

Abstract A cyclic heptapeptide, cyclo-(l-Val-l-Orn-l-Leu-d-Phe-l-Pro-Gly-Gly-), was synthesized in order to investigate a contribution for an antibacterial activity of a ring size of a cyclic peptide. A linear heptapeptide p-nitrophenyl ester, in which an δ-amino function of ornithine residue was protected with benzyloxycarbonyl group, was transformed to the cyclic benzyloxycarbonyl-substituted heptapeptide which was hydrogenated to afford the desired cyclic heptapeptide as hydrochloride. The cyclic peptide thus obtained showed no activity against any of microorganisms tested.