Studies of Peptide Antibiotics. XXVIII. Syntheses of Sesquigramicidin S and Digramicidin S
1973; Oxford University Press; Volume: 46; Issue: 3 Linguagem: Inglês
10.1246/bcsj.46.977
ISSN1348-0634
AutoresShuji Matsuura, Michinori Waki, Tetsuo Kato, Nobuo Izumiya,
Tópico(s)Biochemical and Structural Characterization
ResumoAbstract Two macro-ring analogs of gramicidin S, namely cyclo(–l-Val–l-Orn–l-Leu–d-Phe–l-Pro–)3 (sesquigramicidin S) and cyclo(–l-Val–l-Orn–l-Leu–d-Phe–l-Pro–)4 (digramicidin S), were prepared to investigate the influence of the ring size of gramicidin S for antibacterial activity. Several linear analogs such as H–(l-Val–l-Orn–l-Leu–d-Phe–l-Pro)n–OH (n=2, 3 and 4) were also prepared as reference compounds. All these macroring and linear analogs showed weaker activity than gramicidin S and synergistic property when each of the analogs is mixed with gramicidin S. Measurements of optical rotatory dispersion were made with these analogs and gramicidin S in solvents of ethanol and 8 M aqueous urea. From these experiments, it was suggested that the mode of antibacterial action of the macro-ring analogs and their conformations are similar to those of the linear analogs.
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