Stereoselective epoxidation of phenyl allyl ether by alkene-utilizing bacteria

✍ Scribed by Mahmoud Mahmoudian; Ashour Michael

• Publisher: Springer
• Year: 1992
• Tongue: English
• Weight: 345 KB
• Volume: 37
• Category: Article
• ISSN: 1432-0614
• DOI: 10.1007/bf00174198

✦ Synopsis

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.