Synthesis and properties of gramicidin S analogs containing D-Lys residue in place of Orn residue.

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概要

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• [L-Lys<SUP>2,2′</SUP>]-gramicidin S has been known to possess the same type activity and conformation as that of gramicidin S. The D-isomer of the Lys residue, instead of the Orn residue, was introduced to gramicidin S in order to investigate the contribution of the configurations of the Orn residue in gramicidin S to its activity and conformation. [D-Lys<SUP>2,2′</SUP>]- and [D-Lys<SUP>2</SUP>, L-Lys<SUP>2′</SUP>]-gramicidin S were synthesized by a liquid-phase method. The CD spectra of these analogs showed a pattern similar to that of gramicidin S, suggesting that the conformation of these analogs at the β-turn parts around the D-Phe-Pro sequence resemble that of gramicidin S. These analogs have either a weak or no activity against the Gram-positive microorganisms tested, indicating the importance of the configuration of the Orn residue in gramicidin S for exhibiting strong activity.

• 公益社団法人 日本化学会の論文

著者

• TAMAKI Makoto

  Department of Chemistry, Faculty of Science, Toho University

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