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Biosynthese von Naturstoffen mit einer PC‐Bindung, IX. Synthese und Einbau von ( S )‐ und ( R )‐2‐Hydroxy‐[2‐ 2 H 1 ]ethylphosphonsäure in Fosfomycin durch Streptomyces fradiae
Author(s) -
Hammerschmidt Friedrich
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920196
Subject(s) - chemistry , streptomyces fradiae , stereochemistry , biosynthesis , enzyme , streptomyces , actinomycetales , biochemistry , bacteria , genetics , biology
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.