Stereochemistry of C-3 deoxygenation of sugar nucleosides: formation of pentopyranine C from [3-2H]-D-glucose by Streptomyces griseochromogenes

Abstract

Cytosylglucuronic acid (CGA) has previously been shown to be the first intermediate in the biosynthesis of the antibiotic blasticidin S (BS), produced by Streptomyces griseochromogenes. Addition of aminooxyacetic acid (AOAA), an inhibitor of pyridoxal phosphate/pyridoxamine phsophate-dependent transminases, to S. griseochromogenes fermentations led to substantial accumulations of CGA and pentopyranine C (PPNC, a shunt metabolite which has undergone decarboxylation at C-5', deoxygenation at C-3', and epimerization at C-4') and to substantial reductions in the production of BS and N-demethylBS