The biosynthesis of streptomycin. The origin of the C-formyl group of streptose.
1. The biosynthesis of streptomycin in Streptomyces griseus has been studied by adding d-[3,4-(14)C(2)]glucose or d-[1,3-(14)C(2)]glucose to the growth medium and degrading the streptomycin produced. 2. The results suggest that the C-3' branch carbon atom of l-streptose arises from C-3 of d-glucose. 3. 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.
D000438:Alcohols; D001565:Benzoates; D002247:Carbon Isotopes; D004187:Disaccharides / Q000096:biosynthesis*; D005561:Formates / Q000378:metabolism*; D005947:Glucose / Q000378:metabolism*; D066298:In Vitro Techniques; D013302:Streptomyces / Q000378:metabolism*; D013307:Streptomycin / Q000096:biosynthesis*
D000438:Alcohols; D001565:Benzoates; D002247:Carbon Isotopes; D004187:Disaccharides; D005561:Formates; D005947:Glucose; D013307:Streptomycin
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