title: Bioreduction and disproportionation of cyclohex-2-enone catalyzed by ene-reductase OYE-1 in 'micro-aqueous' organic solvents.
abstract: The bioreduction and disproportionation of cyclohex-2-enone catalyzed by Old Yellow Enzyme 1 was investigated in presence of organic (co)solvents. Whereas the NADH-dependent bioreduction activity strongly decreased at elevated co-solvent concentrations due to the insolubility of the nicotinamide-cofactor, the NADH-free disproportionation was significantly improved in water-immiscible organic co-solvents at 90 % (v/v) with near-quantitative conversion. This positive effect was attributed to removal of the inhibiting co-product, phenol, from the enzyme's active site. The best co-solvents show high lipophilicity (logP) and a high potential to solubilize phenol (Kphenol). As a predictive parameter, the ratio of logP/Kphenol should be preferably ≥100.
authors.affiliation: Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstraße 28, 8010, Graz, Austria.
authors.forename: Dorina
authors.initials: D
authors.lastname: Clay
authors.forename: Christoph K
authors.initials: CK
authors.lastname: Winkler
authors.forename: Gábor
authors.initials: G
authors.lastname: Tasnádi
authors.forename: Kurt
authors.initials: K
authors.lastname: Faber
mesh_terms: D001711:Biotransformation; D003512:Cyclohexanones / Q000378:metabolism*; D009243:NAD / Q000378:metabolism; D009252:NADPH Dehydrogenase / Q000378:metabolism*; D010084:Oxidation-Reduction; D012997:Solvents
chemical_list: D003512:Cyclohexanones; D012997:Solvents; D009243:NAD; C028215:2-cyclohexen-1-one; D009252:NADPH Dehydrogenase