Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Chemical Studies on Blasticidin S Part III
The Structure of Blasticidin S
Noboru OTAKESetsuo TAKEUCHIToyoshige ENDOHiroshi YONEHARA
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1966 年 30 巻 2 号 p. 132-141

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Blasticidin S was cleaved into cytosinine and blastidic acid by acid hydrolysis under selected condition. Chemical and NMR spectral evidences showed that blastidic acid has the structure VI. Alkaline hydrolysis of blasticidin S gave cytomycin which was further degradated into cytosinine and blastidone, whose structure was assigned as 4-ureido-N-methylpiperidone. Hydrogenolyses of blasticidin S and cytomycin afforded the hydro-genolytic compounds SC13 and C13 respectively. SC13 was transformed into C13 by alkali, which was further degradated via partial hydrolysis product PHC13 into 3-aminotetra-hydropyran-2-carboxylic acid and blastidone. The sequence of these reactions established clearily the relationship of degradative compounds and provided evidences to assign struc-ture I and II to blasticidin S and cytomycin respectively.
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© Japan Society for Bioscience, Biotechnology, and Agrochemistry
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