Biosynthese von Naturstoffen mit einer P C‐Bindung, V. Das Oxiran‐Sauerstoff‐Atom des Fosfomycins entstammt nicht dem Luft‐Sauerstoff

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 13CC‐NMR spectrum were prepared starting from Boc‐L‐alaninal. (Z)‐1‐[2,3‐2H2]Propenylphosphonic acid was not incorporated into 1. D‐[6,6‐2H2]Glucose afforded 12 with 16% deuterium at C‐1.