title: Rapid halogen substitution and dibenzodioxin formation during tyrosinase-catalyzed oxidation of 4-halocatechols.
abstract: 4-Fluoro-1,2-benzoquinone, generated by tyrosinase oxidation of 4-fluorocatechol in aqueous buffer, rapidly undergoes substitution by O-nucleophiles (water or catechols) with release of fluoride. 4-Chloro- and 4-bromocatechol behave similarly. The reactions, which have toxicological implications, have been monitored by spectrophotometry and HPLC/MS, and intermediate and final products, including dibenzodioxins, identified.
authors.affiliation: Gray Institute for Radiation Oncology & Biology, University of Oxford, Oxford, UK.
authors.forename: Michael R L
authors.initials: MR
authors.lastname: Stratford
authors.forename: Patrick A
authors.initials: PA
authors.lastname: Riley
authors.forename: Christopher A
authors.initials: CA
authors.lastname: Ramsden
mesh_terms: D016227:Benzoquinones / Q000737:chemistry; D055162:Biocatalysis; D002396:Catechols / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004147:Dioxins / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D013058:Mass Spectrometry; D014442:Monophenol Monooxygenase / Q000378:metabolism*; D010084:Oxidation-Reduction
chemical_list: D016227:Benzoquinones; D002396:Catechols; D004147:Dioxins; D006219:Halogens; C512003:dibenzodioxin; C040660:4-bromocatechol; C072305:4-fluorocatechol; D014442:Monophenol Monooxygenase; C038861:4-chlorocatechol; C025225:2-benzoquinone