title: Preferential oxidative dehalogenation upon conversion of 2-halophenols by Rhodococcus opacus 1G.
abstract: The regiospecificity of hydroxylation of C2-halogenated phenols by Rhodococcus opacus 1G was investigated. Oxidative defluorination at the C2 position ortho with respect to the hydroxyl moiety was preferred over hydroxylation at the non-fluorinated C6 position for all 2-fluorophenol compounds studied. Initial hydroxylation of 2,3, 5-trichlorophenol resulted in the exclusive formation of 3, 5-dichlorocatechol. These results indicate that, in contrast to all other phenol ortho-hydroxylases studied so far, phenol hydroxylase from R. opacus 1G is capable of catalyzing preferential oxidative defluorination but also oxidative dechlorination.
authors.affiliation: Department of Biomolecular Sciences, Laboratory of Biochemistry, Wageningen University, Dreijenlaan 3, 6703 HA, Wageningen, The Netherlands.
authors.forename: V S
authors.initials: VS
authors.lastname: Bondar
authors.forename: M G
authors.initials: MG
authors.lastname: Boersma
authors.forename: W J
authors.initials: WJ
authors.lastname: van Berkel
authors.forename: Z I
authors.initials: ZI
authors.lastname: Finkelstein
authors.forename: E L
authors.initials: EL
authors.lastname: Golovlev
authors.forename: B P
authors.initials: BP
authors.lastname: Baskunov
authors.forename: J
authors.initials: J
authors.lastname: Vervoort
authors.forename: L A
authors.initials: LA
authors.lastname: Golovleva
authors.forename: I M
authors.initials: IM
authors.lastname: Rietjens
mesh_terms: D001673:Biodegradation, Environmental; D002733:Chlorophenols / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003600:Cytosol / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D008861:Microsomes / Q000201:enzymology; D006899:Mixed Function Oxygenases / Q000378:metabolism; D010084:Oxidation-Reduction; D010636:Phenols / Q000378:metabolism*; D012240:Rhodococcus / Q000201:enzymology* / Q000254:growth & development
chemical_list: D002733:Chlorophenols; D010636:Phenols; C056693:2,3,5-trichlorophenol; D006899:Mixed Function Oxygenases; C022336:phenol 2-monooxygenase