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 microg/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.
D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D005578:Fosfomycin / Q000031:analogs & derivatives / Q000096:biosynthesis*; D006880:Hydroxy Acids; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism; D013302:Streptomyces / Q000201:enzymology / Q000378:metabolism*
C531867:2-hydroxybutylphosphonic acid; C531866:2-hydroxyethylphosphonic acid; C531865:2-hydroxypropylphosphonic acid; D004852:Epoxy Compounds; D006880:Hydroxy Acids; D063065:Organophosphonates; D005578:Fosfomycin