Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Chemical Studies on Blasticidin S Part II
The Structure of Cytosinine and Uracinine
Noboru OTAKESetsuo TAKEUCHIToyoshige ENDOHiroshi YONEHARA
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1966 年 30 巻 2 号 p. 126-131

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Acid hydrolysis of cytosinine gave each one mole of cytosine, levulinic acid, ammonia and carbon dioxide. Reduction of cytosinine with PtO2 afforded a mixture of dihydro-cytosinine, 3-amino-tetrahydropyran-2-carboxylic acid and cytosine. Ozonolysis of N, N'-diacetylcytosinine methyl ester, followed by oxidation with hydrogen peroxide and acid hydrolysis gave erythro-D-β-hydroxyaspartic acid. These data permitted the assignment of structure (I) for cytosinine. Acid hydrolysis of uracinine gave uracil instead of cytosine, therefore, the structure (II) could be assigned to uracinine. Some stereochemical features and mechanism of levulinic acid formation were discussed.
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© Japan Society for Bioscience, Biotechnology, and Agrochemistry
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