74 ペプチド系抗生物質アルボペプチンBおよびその類縁体の化学構造(ポスター発表の部)

概要

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New peptide antibiotics named as albopeptins have been isolated from Streptomyces albofaciens. These antibiotics reveal potent antifungal activity against various pathogenetic fungi. The structure of major component albopeptin B (1) has been determined by several spectroscopic method. ^1H- and ^<13>C-NMR spectra indicated that albopeptin B contained two moles of Gly, two moles of dehydrobutyrine (DHB), Val, a modified Cys, an unusual amino acid residue and a ω-substituted fatty acid (3). The structure of 3 was elucidated by the spectroscopic method and it was confirmed by the chemical synthesis. The remained amino acid moiety and the sequence of the amino acid residues were deduced by HMBC and ROESY experiments. The absolute configuration of Val and Ala derived from Cys moiety was determined by Marfey's method. Albopeptin B has two macrocyclic ring which possesses unusual 13-(3'-hydroxyguanido)-tridecanoyl group as a side chain. Minor component (2) is recognized as a deoxy-form of 1 due to MS analysis. Comparison of its ^1H-NMR spectrum to that of 1 showed that the peptide skeleton of two compounds were same and the guanidyl part of the fatty acid on 2 was deoxygenated. Thus, the structure of 2 is determined as N-deoxyalbopeptin B.
天然有機化合物討論会の論文
1992-09-10