Biosynthese von Naturstoffen mit einer PC-Bindung, IX. Synthese und Einbau von (S)- und (R)-2-Hydroxy-[2-2H1]ethylphosphonsäure in Fosfomycin durchStreptomyces fradiae

✍ Scribed by Hammerschmidt, Friedrich

• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: English
• Weight: 469 KB
• Volume: 1992
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199219920196

✦ Synopsis

Biosynthesis of Natural Products with a P—C Bond, IX.— Synthesis and Incorporation of (S)‐ and (R)‐2‐Hydroxy‐[2‐^2^H~1~]ethylphosphonic Acid into Fosfomycin by Streptomyces fradiae

(S)‐ and (R)‐2‐(benzyloxy)‐[1‐^2^H~1~]ethanol (8) were transformed into (S)‐ and (R)‐2‐hydroxy‐[2‐^2^H~1~]ethylphosphonic acid (13). These were fed to cultures of Streptomyces fradiae. The fosfomycin produced was isolated as aminopropylphosphonic acid and contained 32% Deuterium, when (S)‐13 was added to the growth medium, and no deuterium, when the antipode (R)‐13 was added as substrate. The dehydrogenase‐accepting 2‐ hydroxyethylphosphonic acid is stereospecifically removing its pro‐R hydrogen from C‐2.