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Biosynthese von Naturstoffen mit einer P C‐Bindung, V. Das Oxiran‐Sauerstoff‐Atom des Fosfomycins entstammt nicht dem Luft‐Sauerstoff
Author(s) -
Hammerschmidt Friedrich,
Bovermann Günter,
Bayer Karl
Publication year - 1990
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.1990199001191
Subject(s) - chemistry , streptomyces fradiae , diastereomer , fosfomycin , medicinal chemistry , stereochemistry , nuclear chemistry , organic chemistry , streptomyces , bacteria , actinomycetales , genetics , biology , antimicrobial
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 18 O 2 ‐enriched atmosphere produced unlabelled fosfomycin. For comparison 18 O‐labelled diastereomeric (2‐amino‐1‐hydroxypropyl)phosphonic acids 16 and 17 showing an α shift of 0.025 ppm in the 13C C‐NMR spectrum were prepared starting from Boc‐L‐alaninal. ( Z )‐1‐[2,3‐ 2 H 2 ]Propenylphosphonic acid was not incorporated into 1 . D‐[6,6‐ 2 H 2 ]Glucose afforded 12 with 16% deuterium at C‐1.