Synthetic studies on quinoxaline antibiotics. III. Synthesis of nortriostin A, a triostin A analog lacking N-methyl groups on the cystine and valine residues.
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概要
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Nortriostin A, which is an analog of a cyclic octadepsipeptide antibiotic triostin A and contains one cystine and two valine residues substituted for the <I>N</I>,<I>N</I>′-dimethylcystine and <I>N</I>-methylvaline residues of the antibiotic, was synthesized with Z–D-Ser[Boc–Ala–Cys(MeBzl)–Val]–OH and Z–D-Ser[H–Ala–Cys(MeBzl)–Val]–OTce as key intermediates. The synthetic analog showed no antimicrobial activity at a concentration of 100 μg/ml and was found to exist as a single structure in solution as examined by <SUP>1</SUP>H-NMR spectroscopy. The latter observation suggests that the conformer equilibrium known to occur with triostin A is a consequence of the presence of <I>N</I>-methyl peptide bonds in the antibiotic molecule.
- 公益社団法人 日本化学会の論文
著者
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Kyogoku Yoshimasa
Institute For Protein Research Osaka University
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Shin Masaru
Shionogi Research Laboratories Shionogi & Co. Ltd.
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Higuchi Naoki
Institute For Fundamental Research Suntory Ltd.
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Inouye Ken
Shionogi Research Laboratories, Shionogi & Co., Ltd.
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Shin Masaru
Shionogi Research Laboratories, Shionogi & Co., Ltd.
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SHIN Masaru
Shionogi Laboratories, Shionogi and Co., Ltd.
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Higuchi Naoki
Institute for Protein Research, Osaka University
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