On the conversion of structural analogues of (S)-2-hydroxypropylphosphonic acid to epoxides by the final enzyme of fosfomycin biosynthesis in S. fradiae

2-Hydroxyethyl- and (S)-2-hydroxybutylphosphonic acid were prepared, starting in the latter case from (S)-2-aminobutyric acid. They were fed to cultures of Streptomyces fradiae producing fosfomycin. Only the latter (150 μg/mL of medium) was converted to the ethyl analogue of fosfomycin, isolated as 2-amino-1-hydroxybutylphosphonic acid (3%) in admixture with 2-amino-1-hydroxypropylphosphonic acid (97%) derived from fosfomycin.

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