Stereoselective epoxidation of cis-propenylphosphonic acid to fosfomycin by a newly isolated bacterium Bacillus simplex strain S101.
In industry, fosfomycin is mainly prepared via chemical epoxidation of cis-propenylphosphonic acid (cPPA). The conversion yield of fosfomycin is less than 50% in the whole process and a large quantity of waste is produced. Biotransformation by microorganisms is an alternative method of preparation. This kind of conversion is more delicate, environmentally friendly, and the conversion yield of fosfomycin would be higher. In this work, an aerobic bacterium capable of transforming cPPA to fosfomycin was isolated. The organism, designated as strain S101, was identified as Bacillus simplex by morphological and physiological characteristics as well as by analysis of the gene encoding the 16S rRNA. Fosfomycin was assayed by two means, bioassay and gas chromatography (GC). Glycerol was a good carbon source for growth and cPPA conversion of strain S101. When cPPA was used as the sole carbon source, neither growth nor conversion to fosfomycin occurred. The optimum cPPA concentration in the conversion medium was 2,000 microg ml(-1). After 6 days of incubation, the concentration of fosfomycin reached its maximum level (1,838.2 microg ml(-1)), with a conversion ratio of 81.3%. Air was indispensable for the growth but not for the conversion to fosfomycin. Furthermore, vanadium ions were found to be essential for the conversion. High concentrations of cPPA had fewer inhibitory effects on the growth of strain S101.
Xie
Fuhong
F
State Key Laboratories of Transducer Technology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China.
Chao
Yapeng
Y
Xue
Zhiquan
Z
Yang
Xiuqing
X
Zhang
Guoqing
G
Shi
Jiaji
J
Qian
Shijun
S
D001407:Bacillus / Q000145:classification / Q000235:genetics / Q000302:isolation & purification* / Q000378:metabolism*; D001711:Biotransformation; D004269:DNA, Bacterial / Q000235:genetics; D004275:DNA, Ribosomal / Q000235:genetics; D004852:Epoxy Compounds / Q000378:metabolism*; D005578:Fosfomycin / Q000737:chemistry / Q000378:metabolism*; D008969:Molecular Sequence Data; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000378:metabolism*; D010802:Phylogeny; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D012988:Soil Microbiology; D013237:Stereoisomerism
D004269:DNA, Bacterial; D004275:DNA, Ribosomal; D004852:Epoxy Compounds; D009943:Organophosphorus Compounds; D012336:RNA, Ribosomal, 16S; C074765:propenylphosphonic acid; D005578:Fosfomycin