Synthesis and Properties of Gramicidin S Analogs Containing Pro–d-Phe Sequence in Place of d-Phe–Pro Sequence in the β-Turn Part of the Antibiotic
- 1 May 1985
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 58 (5) , 1469-1472
- https://doi.org/10.1246/bcsj.58.1469
Abstract
Two analogs of gramicidin S, [l-Pro4, d-Phe5]-gramicidin S and [l-Pro4,4′, d-Phe5,5′]-gramicidin S, were synthesized in order to investigate the relationships among positions of Pro residues, antibiotic activity and CD spectra. [l-Pro4,4′, d-Phe5,5′]-gramicidin S showed little activity. On the other hand, the activity of [l-Pro4, d-Phe5]-gramicidin S against Bacillus subtilis and Micrococcus flavus was the same as that of gramicidin S, and its activity toward other microorganisms tested was 1/2 that of gramicidin S. The CD spectra of these analogs and gramicidin S in an aqueous solution differ from each other, indicating that these peptides have different conformations in aqueous solutions. The CD spectrum of [l-Pro4, d-Phe5]-gramicidin S resembles a graphical average of the CD spectra of gramicidin S and [l-Pro4,4′, d-Phe5,5′]-gramicidin S.This publication has 7 references indexed in Scilit:
- Synthesis and Properties of Gramicidin S Analogs Containing d-Phe–l-Pro–d-Val or l-Phe–l-Pro–d-Val Sequences in Place of d-Phe–l-Pro–l-Val Sequence in the β-Turn Part of the AntibioticBulletin of the Chemical Society of Japan, 1985
- Studies on Peptide Antibiotic “Gratisin”Bulletin of the Chemical Society of Japan, 1984
- Natural homologs of gramicidin S.The Journal of Antibiotics, 1984
- Studies on the β-Turn of Peptides. VII. Syntheses and Antibiotic Activities of Gramicidin S Analogs with l-Pro-l-Asn or l-Pro-d-Ala Sequence at the β-Turn PartBulletin of the Chemical Society of Japan, 1983
- Synthesis of [4-5,4′-5′-Bis(δ-Aminovaleric Acid)]-Gramicidin SBulletin of the Chemical Society of Japan, 1975
- A NEW SYNTHETIC AND ANTIBIOTIC ANALOG OF GRAMICIDIN S, [4-5-δ-AMINOVALERIC ACID]-GRAMICIDIN SThe Journal of Antibiotics, 1972
- Appendix 2—Possible molecular models for gramicidin S and their relationship to present ideas of protein structureBiochemical Journal, 1957