Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies of Peptide Antibiotics. VI. Syntheses of Cyclic Penta and Decapeptides with a Glycyl-L-ornithyl-L-leucyl-D-phenylalanylglycyl Sequence
Michio KondoHaruhiko AoyagiTetsuo KatoNobuo Izumiya
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1966 Volume 39 Issue 10 Pages 2234-2242

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Abstract

A cyclic decapetide dihydrochloride, cyclo-(glycyl-L-ornithyl-L-leucyl-D-phenylalanylglycyl)2·2HCl, which is an analog of gramicidin S, and a cyclic pentapetide monohydrochloride, cycloglycyl-L-ornithyl-L-leucyl-D-phenylalanylglycyl·HCl,where synthesized in order to compare their decapeptide active esters was found to yield the same cyclic bezyloxycarbonyl-substiuted decapetide: this was converted by hydrogenolysis to the cyclic decapeptide dihydrochloride mentioned above. The cyclization reaction of a linear pentapetide active ester, in which the glycines are both terminal amino acid residues, yielded a cyclic benzyloxycarbonyl-substiuted pentapetide exclusively. When another linear pentapeptide active ester and a pentapetide azide where also subjected to cyclization reaction, they afforded the same cyclic benzyloxycarbonylsubstituted pentapeptide; this was then hydrogenolyzed to the corresponding cyclic pentapeptide monohydrochloride. The effects of the two cyclic peptide hydrochlorides on the bacterial growth were tested; no retardation of growth was observed with any of the microorganisms tested.

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