Studies of Peptide Antibiotics. XIX. Syntheses of 1,1′-Leucine-gramicidin S and 1-Leucine-cyclosemigramicidin S
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Analogs of gramicidin S, 1,1′-L-leucine-gramicidin S (XI) and 1-L-leucine-cyclosemigramicidin S (XII), have been synthesized and tested for antibacterial properties. The cyclization reaction of a linear decapeptide active ester, in which δ-amino functions of ornithine residues were protected with benzyloxycarbonyl groups, yielded exclusively a protected cyclic decapeptide which was hydrogenated to afford the dihydrochloride of XI. A linear pentapeptide active ester afforded a mixture of protected cyclic penta and decapeptide. The pure protected cyclic pentapeptide was obtained with the use of a Sephadex LH-20 column, and the hydrogenolysis of the product afforded the hydrochloride of XII. The decapeptide analog (XI) was as active as natural gramicidin S, whereas the pentapeptide (XII) showed no activity toward any of the microorganisms tested.
- 公益社団法人 日本化学会の論文
著者
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Izumiya Nobuo
Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University
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Kondo Michio
Department Of Chemistry Faculty Of Science And Ehgineering Saga University
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