Stereoselective epoxidation of phenyl allyl ether by alkene-utilizing bacteria.
Eighteen newly isolated ethene- and propene-utilizing bacteria were screened for the ability to produce phenyl glycidyl ether, a common precursor for the synthesis of beta blockers, from phenyl allyl ether. These organisms included Aerococcus, Alcaligenes, Micrococcus and Staphylococcus spp. and a variety of Gram-negative, Gram-positive and Gram-variable mesophilic rods/coccobacilli not yet identified. The majority of ethene- and propene-grown cultures (14 strains) accumulated phenyl glycidyl ether (0.4-1.7 mM) as the sole oxidation product. The bioconversions with the three most promising ethene-utilizers (M26, M90C, M93A) were scaled-up to yield essentially optically pure (enantiomeric excess = 93%) S-(+)-phenyl glycidyl ether. This is currently under investigation for commercial production of optically pure beta blockers.
Mahmoudian
M
M
Centre for Biotechnology, Imperial College of Science, Technology and Medicine, London, UK.
Michael
A
A
D000475:Alkenes / Q000378:metabolism; D000498:Allyl Compounds / Q000378:metabolism*; D001419:Bacteria / Q000378:metabolism*; D004852:Epoxy Compounds / Q000378:metabolism; D010647:Phenyl Ethers / Q000378:metabolism*; D013237:Stereoisomerism
D000475:Alkenes; D000498:Allyl Compounds; D004852:Epoxy Compounds; D010647:Phenyl Ethers; C076695:phenyl allyl ether; C016050:phenylglycidyl ether