Biosynthesis of natural products with a P–C bond. Part 8: on the origin of the oxirane oxygen atom of fosfomycin in Streptomyces fradiae

• DOI: 10.1039/p19910001993
• Publication Date: 2004-04-26T11:12:20Z
• Authors: Friedrich Hammers...
• Keywords: Fosfomycin; Streptomyces fradiae

(R, S)-, (R)- and (S)-(2-Hydroxy-[1, 1-2H2]propyl)phosphonic acid were fed to Streptomyces fradiae producing fosfomycin isolated as the corresponding ring-opened aminophosphonic acid. Only (S)(2-hydroxy-[1,1-2H2]propyl)phosphonic was efficiently incorporated into (37% deuterium at C-1 of acid). (R,S)-(2-[18O]Hydroxypropyl)phosphonic gave [1-18O]aminophosphonic None four stereoisomeric (1,2-dihydroxy-[1-2H1]propyl)phosphonic acids labelled fosfomycin. Both (1R,2S)- (1S,2S)-(1,2-dihydroxy-[1-3H]propyl)phosphonic taken up cells, but not specifically fosfomycin, dilution radioactivity being 0.02 0.01%, respectively. Obviously they are intermediates biosynthesis