Abstract
Fifteen strains of aerobic bacteria and two actinomycetous strains were isolated from various soil samples, using cis-propenylphosphonic acid as the sole source of carbon. Taxonomic studies showed that these belonged to the Pseudomonas, Alcaligenes, Flavobacterium, Aeromonas, Corynebacterium and Streptomyces genera. Most of these strains produced the antibiotic fosfomycin [(-)-(1R, 2S)-1,2-epoxypropylphosphonic acid] from cis-propenylphosphonic acid by stereoselective epoxidation. Under the culture conditions tested, the production of fosfomycin reached a level of 2.0 mg/ml and 0.75 mg/ml by F. esteroaromaticum IFO 3751 and P. putida IK-8 respectively. Purified fosfomycin was an active stereoisomer and its optical purity was a little higher than that of the synthetic compound. Although the stereoespecificity of each enzyme participating in the epoxidation reaction has not yet been clarified, the epoxide formation proceeded through a bromohydrin intermediate produced by bromoperoxidase, finally yielding fosfomycin by the action of halohydrin epoxidase.
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Itoh, N., Kusaka, M., Hirota, T. et al. Microbial production of antibiotic fosfomycin by a stereoselective epoxidation and its formation mechanism. Appl Microbiol Biotechnol 43, 394–401 (1995). https://doi.org/10.1007/BF00218439
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DOI: https://doi.org/10.1007/BF00218439