The biosynthesis of streptomycin. The origin of the C-formyl group of streptose

Abstract

The biosynthesis of streptomycin in Streptomyces griseus has been studied by adding D-[3,4-14C2]glucose or D-[1,3-14C2] glucose to the growth medium and degrading the streptomycin produced. The results suggest that the C-3[image] branch carbon atom of L-streptose arises from C-3 of D-glucose. The mechanism of biosynthesis of streptose from glucose is discussed. It probably involves an intramolecular rearrangement of a 6-deoxy-4-oxyhexose derivative, and it is suggested that the nucleoside diphosphate sugar derivative hitherto recognized as an intermediate in the biosynthesis of L-rhamnose might participate in such a rearrangement.