Incorporation of  L ‐[Methyl‐ 2 H 3 ]methionine and 2‐[Hydroxy‐ 18 O]hydroxyethylphosphonic Acid into Fosfomycin in  Streptomyces fradiae —An Unusual Methyl Transfer | Zendy

Hammerschmidt Friedrich | Zendy

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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.

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