Biosynthesis of Natural Products with a P-C Bond, V. - The Oxirane Oxygen Atom of Fosfomycin Is not Derived from Atmospheric Oxygen
Fosfomycin (1) in the culture broth of Streptomyces fradiae was transformed into (amino-hydroxypropyl)phosphonic acids 12 and 13.The main product 12 was isolated by ion-exchange chromatography.Streptomyces fradiae grown in an 18O2-enriched atmosphere produced unlabelled fosfomycin.For comparison 18O-labelled diastereomeric (2-amino-1-hydroxypropyl)phosphonic acids 16 and 17 showing an α shift of 0.025 ppm in the 13C-NMR spectrum were prepared starting from Boc-L-alaninal. (Z)-1-Propenylphosphonic acid was not incorporated into 1.D-Glucose afforded 12 with 16percent deuterium at C1.
Hammerschmidt, Friedrich,Bovermann, Guenther,Bayer, Karl
p. 1055 - 1061
(2007/10/02)
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