Absolute configuration of blasticidin S

✍ Scribed by Hiroshi Yonehara; Noboru Ōtake

• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 269 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99967-8

✦ Synopsis

In the works on the chemistry of blasticidln S (I), a methabollte.of Streotomyces griseochromogenes, we have demonstrated its unique structural feature which consists of a new nucleoslde cytosinine (II) ana a new amino acid, blastiaic 1-4 acid (III) on the basis of chemical reactions and spectral evidences. Taking account of various biological activities together with the biogenetic interest of the antibiotic, the absolute configuration of I has to be made clear. Thls communication deals with chemical evidences which allow the assignment of a P-configuration to the anomeric center in II and sn L-configuration to the amino acid (III); consequently, the absolute configuration can be represented by 1: II was esterified with methanolic hydrogen chloride to the methyl ester alhydrochloride' (IV), which was converted to the * These data were reported at the Svmooslum on the Phvslolopicallv Active Substances and Natural Products, the Annual Meeting of the Agricultural Chemical Society of'Japan held in Kyoto, April 2, 1966.