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Incorporation of L ‐[Methyl‐ 2 H 3 ]methionine and 2‐[Hydroxy‐ 18 O]hydroxyethylphosphonic Acid into Fosfomycin in Streptomyces fradiae —An Unusual Methyl Transfer
Author(s) -
Hammerschmidt Friedrich
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199403411
Subject(s) - streptomyces fradiae , fosfomycin , methionine , methylation , biosynthesis , chemistry , methyl group , stereochemistry , antibiotics , biochemistry , group (periodic table) , streptomyces , amino acid , biology , bacteria , organic chemistry , dna , enzyme , actinomycetales , genetics
A novel “methylation” takes place in the biosynthesis of the antibiotic fosfomycin: apparently a methyl group from L ‐methionine adds to phosphonoacetaldehyde ( 1 ) as “CH 3 − ” to provide ( S )‐2‐hydroxypropylphosphonic acid ( 2 ). In contrast, ( S )‐adenosylmethionine transfers formally CH 3 +in a different manner.