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Structure of cytosinine, a structural component of blasticidin s

✍ Scribed by Noboru Ōtake; Setsuo Takeuchi; Toyoshige Endō; Hiroshi Yonehara

Publisher: Elsevier Science
Year: 1965
Tongue: French
Weight: 176 KB
Volume: 6
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)90079-0

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✦ Synopsis

In previous papers"', we have reported the isolation and characterization of a new nucleoside designated cytosinine from the hydrolysis products of blasticidin.S, a useful antibiotic against rice blast desease. We wish to present the details leading to the assignment of structure I to cytosinine. Cytosinine (I), Cj0H1s04N4, m.p. 244-245O, [aJL8-20°(c, 1 in H*O), pKa 2.4, 4.6 and 8.0,~$2?@ 274 mi* (6 13,800), nO$$OH 267 rnp (& 7,500), showed the existence of two ethylenic groups (NMR (in DZO) ppm: 7.72 and 6.14 (2H d, AB type, J = 7.5 cps) and 6.45-6.00 (2H broad)), two amino groqs (Van Slyke determination) and one csrboxylic group. By the action of methanol containing 3% hydrogen chloride, I gave corresponding methyl ester dihydrochloride, C,oHsOsN4(0CHs)*2HCl,

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