Studies of Peptide Antibiotics. X. Syntheses of Cyclosemigramicidin S and Gramicidin S
- 1 July 1967
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 40 (7) , 1687-1692
- https://doi.org/10.1246/bcsj.40.1687
Abstract
The possibility of the occurrence of benzyloxycarbonyl-substituted cyclosemigramicidin S in the course of the cyclization reaction of a linear-pentapeptide-active ester with pyridine was investigated. It was indicated that the crude product of the cyclization of the linear-active ester was composed of two components. The protected gramicidin S, a less soluble material, was easily isolated by fractional crystallization, while the protected cyclosemigramicidin S, a more soluble material, was isolated by a column chromatography of Sephadex LH-20. The hydrogenolyses of these products in the presence of hydrogen chloride afforded the crystalline hydrochlorides of gramicidin S and cyclosemigramicidin S. The cyclic decapeptide was as active as the natural gramicidin S, however, cyclosemigramicidin S showed no activity in response to any of the microorganisms tested.This publication has 14 references indexed in Scilit:
- Studies of Peptide Antibiotics. IX. Synthesis of cyclo-(l-Valyl-l-ornithyl-l-leucyl-d-phenylalanyl-glycyl)Bulletin of the Chemical Society of Japan, 1967
- Studies of Peptide Antibiotics. VIII. Synthesis of Gly4,4′-gramicidin SBulletin of the Chemical Society of Japan, 1967
- Cyclosemigramicidin SJournal of the American Chemical Society, 1967
- Studies of Peptide Antibiotics. VI. Syntheses of Cyclic Penta and Decapeptides with a Glycyl-l-ornithyl-l-leucyl-d-phenylalanylglycyl SequenceBulletin of the Chemical Society of Japan, 1966
- IUPAC-IUB Commission on Biochemical Nomenclature. Abbreviated Designation of Amino Acid Derivatives and Peptides. Tentative Rules*Biochemistry, 1966
- Studies of Peptide Antibiotics. V. Syntheses of Cyclic Penta- and Decapeptides with the l-Valyl-l-ornithyl-l-leucyl-d-phenylalanylsarcosyl SequenceBulletin of the Chemical Society of Japan, 1966
- Cyclo-(L-valyl-L-ornithyl-L-leucyl-D-phenylalalanylglycyl)2, an Active Analog of Gramicidin SJournal of the American Chemical Society, 1964
- Verwendung farbiger Schutzgruppen zur Synthese von bis‐homo‐Gramicidin SHelvetica Chimica Acta, 1960
- Verdoppelungsreaktionen beim Ringschluss von Peptiden. I. Synthese von Gramicidin S und von bis‐homo‐Gramicidin S aus den Pentapeptid‐Einheiten. 7. Mitteilung über homodet cyclische PolypeptideHelvetica Chimica Acta, 1958
- Die Synthese von Gramicidin SHelvetica Chimica Acta, 1957