title: Whole-cell oxidation of omeprazole sulfide to enantiopure esomeprazole with Lysinibacillus sp. B71.
abstract: Production of enantiopure esomeprazole by biocatalysis is of great demand by pharmaceutical industry. A Gram-positive bacterium oxidizing omeprazole sulfide 1a (5-methoxy-2-[((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio]-1H-benzoimidazole) to (S)-sulfoxide esomeprazole 2a (S)-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl) methylsulfinyl]-3H-benzoimidazole was isolated from soil polluted with elemental sulfur. The strain exhibited the highest identity with the genus Lysinibacillus and catalyzed oxidation of 1a into enantiopure esomeprazole with conversion of 77% in a stirred bioreactor, fed-batch culture. No consecutive oxidation of (S)-sulfoxide to sulfone was observed during whole-cell catalysis. The unique characteristics of the catalyst provide a solid basis for further improvement and development of sustainable green bioprocess.
authors.affiliation: Laboratory of Enzyme Technology, Institute of Microbiology, v.v.i., Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20 Prague 4, Czech Republic.
authors.forename: Peter
authors.initials: P
authors.lastname: Babiak
authors.forename: Eva
authors.initials: E
authors.lastname: Kyslíková
authors.forename: Václav
authors.initials: V
authors.lastname: Stěpánek
authors.forename: Renáta
authors.initials: R
authors.lastname: Valešová
authors.forename: Andrea
authors.initials: A
authors.lastname: Palyzová
authors.forename: Helena
authors.initials: H
authors.lastname: Marešová
authors.forename: Josef
authors.initials: J
authors.lastname: Hájíček
authors.forename: Pavel
authors.initials: P
authors.lastname: Kyslík
mesh_terms: D001407:Bacillus / Q000378:metabolism*; D001483:Base Sequence; D019149:Bioreactors; D001711:Biotransformation; D002855:Chromatography, Thin Layer; D003470:Culture Media; D017931:DNA Primers; D064098:Esomeprazole; D006863:Hydrogen-Ion Concentration; D009853:Omeprazole / Q000031:analogs & derivatives* / Q000378:metabolism*; D010084:Oxidation-Reduction; D016133:Polymerase Chain Reaction; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D003470:Culture Media; D017931:DNA Primers; C040449:omeprazole sulfide; D009853:Omeprazole; D064098:Esomeprazole