Microbial epoxidation of cis-propenylphosphonic to (-)-cis-1,2-epoxypropylphosphonic acid.
Eighteen species of Penicillium, one of Oidium and one of Paecilomyces were found to effect a stereospecific conversion of cis-propenylphosphonate to fosfomycin which was identified by paper chromatography and gas-liquid chromatography (GLC) of the trimethylsilyl esters. Penicillium spinulosum carried out the epoxidation only after the glucose substrate had been utilized. Glucose controlled the epoxidation since its residual concentrations in the broth severely depresses the reaction. At optimum levels of glucose, an epoxidation efficiency approaching 90% of olefin charged (0.2 g/liter) was obtained after 10 days of incubation. The olefin concentration could be increased to 0.5 g/liter when glucose was replaced by glycerol, whereby a 90% conversion to fosfomycin was attainable in 6 days. The high conversion efficiency, a good agreement between the GLC assay and bioactivity, are indicative of the levorotatory nature of the product.
D000475:Alkenes / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000032:analysis / Q000096:biosynthesis*; D001681:Biological Assay; D050260:Carbohydrate Metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002854:Chromatography, Paper; D003470:Culture Media; D004988:Ethers, Cyclic / Q000096:biosynthesis*; D005285:Fermentation; D005947:Glucose / Q000378:metabolism; D005990:Glycerol / Q000378:metabolism; D003904:Mitosporic Fungi / Q000254:growth & development / Q000378:metabolism*; D063065:Organophosphonates / Q000378:metabolism*; D010407:Penicillium / Q000254:growth & development / Q000378:metabolism*; D011511:Proteus; D013237:Stereoisomerism
D000475:Alkenes; D000900:Anti-Bacterial Agents; D003470:Culture Media; D004988:Ethers, Cyclic; D063065:Organophosphonates; D005947:Glucose; D005990:Glycerol