In order to investigate a contribution for an antibacterial activity of a direction of the peptide bonds in gramicidin S molecule, retrogramicidin S with the reverse peptide sequence was prepared through a cyclization reaction of linear decapeptide active ester in pyridine. The cyclization of linear pentapeptide active ester yielded a mixture of retrocyclosemigramicidin S and retrogramicidin S. Retrogramicidin S thus obtained exhibited a weak activity against Bacillus subtilis and Staphylococcus aureus, whereas retrocyclosemigramicidin S showed no activity against any of microorganisms tested.
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Waki et al. (1968) studied this question.
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