Natural homologs of gramicidin S. II. Synthesis of gramicidin S-2 and S-3.

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概要

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• Two cyclic dodecapeptides corresponding to newly found members of gramicidin S family, gramicidin S-2: <I>cyclo</I>(–Val–Orn–Leu–D-Phe–Pro–Abu–Orn–Leu–D-Phe–Pro–), and gramicidin S-3: <I>cyclo</I>(–Abu–Orn–Leu-D-Phe–Pro–Abu–Orn–Leu–D-Phe–Pro–), were synthesized. In the synthesis, the linear decapeptide precursors of the antibiotics prepared by a combination of the "hold-in-solution" method and the usual liquid phase method were converted to cyclic ones in excellent yields by one-pot reaction using 1-ethyl-3-(3-dimethylaminopropyl)carbo-diimide hydrochloride and 1-hydroxybenzotriazole. The synthesized antibiotics were identical with the natural products in HPLC analysis and assays of the antibiotic activities. The proposed structures for gramicidin S-2 and S-3 were confirmed. The CD spectra showed that the ring conformations of gramicidin S-2 and S-3 closely resemble each other and also that of gramicidin S-1, which has the already known structure.

• 公益社団法人 日本化学会の論文

著者

• Muramatsu Ichiro

  Department Of Chemistry College Of Science Rikkyo University

• Nozaki Sukekatsu

  Faculty Of Pharmaceutical Sciences Josai University

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• Natural homologs of gramicidin S. II. Synthesis of gramicidin S-2 and S-3.
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