Studies on the biosynthesis of blasticidin S. V. Isolation and structure of pentopyranic acid.

The Journal of Antibiotics
1976.0

Abstract

In the course of studies on the biosynthesis of blasticidin S, a nucleoside antibiotic, we have isolated six novel cytosine nucleosides, named pentopyranines A to F, from the fermentation broth of Streptomyces griseochromogenes. The structural relationship between these nucleosides and cytosinine (the nucleoside moiety of blasticidin S) implied the intermediacy of cytosine nucleosides with a hexuronic acid moiety in the biosynthesis of blasticidin S. Accordingly, we succeeded in isolating a cytosine nucleoside designated pentopyranic acid (I) from the amphoteric fraction of the fermentation broth of S. griseochromogenes. Through analyses including UV, 1H-nmr, mass, CD spectra, and comparison with an authentic sample, the structure of I was determined to be 1-(β-D-glucopyranosyluronic acid)-cytosine. The isolation of I is taken as evidence that it is the direct precursor of the hypothetical intermediate X in blasticidin S biosynthesis and that the oxidation of the hydroxymethyl group of the hexose moiety takes place prior to that at C-4.

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