Studies of Peptide Antibiotics. XL Analogs of Gramicidin S and Cyclosemigramicidin S Containing Glycine or Alanine in Place of Valine
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- Kondo Michio
- Laboratory of Biochemistry, Faculty of Science, Kyushu University
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- Izumiya Nobuo
- Laboratory of Biochemistry, Faculty of Science, Kyushu University
Description
To investigate the contribution for the antibacterial activity of the valine residues in a gramicidin S molecule, two analogs of gramicidin S, 1, 1′-glycine- and 1, 1′-L-alanine-gramicidin S, were prepared through the cyclization reaction of linear decapeptide active esters in pyridine. 1-Glycine- and 1-L-alanine-cyclosemigramicidin S were also prepared through the cyclization of linear pentapeptide active esters. The effects of the four cyclic peptides thus obtained on bacterial growth were tested; only 1, 1′-alanine-gramicidin S was as active as natural gramicidin S, while the other three analogs showed no activity in relation to any of the microorganisms tested. The results indicate that the side chains of the valines in gramicidin S can be replaced by smaller aliphatic side chains, the methyls, without the influence for the activity.
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 40 (8), 1975-1980, 1967
The Chemical Society of Japan
