title: Monohydroxylation of phenol and 2,5-dichlorophenol by toluene dioxygenase in Pseudomonas putida F1.
abstract: Pseudomonas putida F1 contains a multicomponent enzyme system, toluene dioxygenase, that converts toluene and a variety of substituted benzenes to cis-dihydrodiols by the addition of one molecule of molecular oxygen. Toluene-grown cells of P. putida F1 also catalyze the monohydroxylation of phenols to the corresponding catechols by an unknown mechanism. Respirometric studies with washed cells revealed similar enzyme induction patterns in cells grown on toluene or phenol. Induction of toluene dioxygenase and subsequent enzymes for catechol oxidation allowed growth on phenol. Tests with specific mutants of P. putida F1 indicated that the ability to hydroxylate phenols was only expressed in cells that contained an active toluene dioxygenase enzyme system. 18O2 experiments indicated that the overall reaction involved the incorporation of only one atom of oxygen in the catechol, which suggests either a monooxygenase mechanism or a dioxygenase reaction with subsequent specific elimination of water.
authors.affiliation: Air Force Engineering and Services Laboratory, Tyndall Air Force Base, Florida 32403.
authors.forename: J C
authors.initials: JC
authors.lastname: Spain
authors.forename: G J
authors.initials: GJ
authors.lastname: Zylstra
authors.forename: C K
authors.initials: CK
authors.lastname: Blake
authors.forename: D T
authors.initials: DT
authors.lastname: Gibson
mesh_terms: D002396:Catechols / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D002733:Chlorophenols / Q000378:metabolism*; D002849:Chromatography, Gas; D004790:Enzyme Induction; D006900:Hydroxylation; D013058:Mass Spectrometry; D009154:Mutation; D010101:Oxygen Consumption; D010105:Oxygenases / Q000378:metabolism*; D019800:Phenol; D010636:Phenols / Q000378:metabolism*; D011549:Pseudomonas / Q000201:enzymology* / Q000235:genetics
chemical_list: D002396:Catechols; D002733:Chlorophenols; D010636:Phenols; D019800:Phenol; C056892:2,5-dichlorophenol; D010105:Oxygenases; C023172:toluene dioxygenase