Scale-up of Baeyer-Villiger monooxygenase-catalyzed synthesis of enantiopure compounds.
Several Baeyer-Villiger monooxygenases converting a wide spectrum of substrates have been discovered, cloned, and characterized throughout the last few years. Still, only a few of them are applicable for large-scale conversion predominantly due to their sensitivity towards high substrate and/or product concentrations. The recently cloned and characterized 4-hydroxyacetophenone monooxygenase from Pseudomonas putida JD1 shows excellent enantioselectivity towards 3-phenyl-2-butanone with E > 100 but is inhibited by concentrations >10 mM of both substrate and product. This obstacle could be circumvented by in situ substrate feed and product removal using a hydrophobic Lewatit® adsorbent resin. Thus, the concentration of 3-phenyl-2-butanone could be increased from 1.4 to >26 mM without significant reduction in conversion.
Geitner
Kristian
K
Department of Biotechnology and Enzyme Catalysis, Institute for Biochemistry, Greifswald University, Germany.
Rehdorf
Jessica
J
Snajdrova
Radka
R
Bornscheuer
Uwe T
UT
D055162:Biocatalysis; D001709:Biotechnology; D002074:Butanones / Q000737:chemistry / Q000378:metabolism*; D004926:Escherichia coli / Q000201:enzymology / Q000235:genetics / Q000378:metabolism; D007218:Industrial Microbiology / Q000379:methods; D053858:Metabolic Networks and Pathways; D006899:Mixed Function Oxygenases / Q000737:chemistry / Q000378:metabolism*; D009249:NADP / Q000378:metabolism; D010084:Oxidation-Reduction; D010105:Oxygenases / Q000378:metabolism*; D016958:Pseudomonas putida / Q000201:enzymology* / Q000378:metabolism; D012117:Resins, Synthetic; D013237:Stereoisomerism; D013379:Substrate Specificity
D002074:Butanones; D012117:Resins, Synthetic; D009249:NADP; D006899:Mixed Function Oxygenases; D010105:Oxygenases; C427385:4-hydroxyacetophenone monooxygenase