Studies of Peptide Antibiotics. XXX. Syntheses of Gramicidin S Analogs Containing <I>N</I>-Methylleucine in Place of Leucine

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概要

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• Two analogs of gramicidin S, <I>cyclo</I>(–Val–Orn–Leu–D-Phe–Pro–Val–Orn–MeLeu–D-Phe–Pro–), <I>i.e.</I>, [3-<I>N</I>-Methylleucine]–gramicidin S, and <I>cyclo</I>(–Val–Orn–MeLeu–D-Phe–Pro–Val–Orn–MeLeu–D-Phe–Pro–), <I>i.e.</I>, [3,3′-di-<I>N</I>-Methylleucine]–gramicidin S, were prepared in an attempt to investigate the contribution of the NH group of the leucine residue with regard to antibacterial activity. These analogs were almost as active as gramicidin S in the antibacterial test in reaction to microorganisms. The optical rotatory dispersions of these two analogs and of gramicidin S were measured in solvents of ethanol and 8 M aqueous urea. These studies suggested that both of the analogs containing <I>N</I>-methylleucine have a molecular conformation very similar to that of gramicidin S, and that the NH group of the leucine residues is not necessary for stabilizing the conformation in order to exhibit the biological properties.

• 公益社団法人 日本化学会の論文

著者

• Izumiya Nobuo

  Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University

• Sugano Hiroshi

  Department Of Biochemistry Faculty Of Science Niigata University

• Abe Hayao

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

• Kato Tetsuo

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

• Miyoshi Muneji

  Department of Synthetic Chemistry, Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

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