Rapid halogen substitution and dibenzodioxin formation during tyrosinase-catalyzed oxidation of 4-halocatechols.

Journal article

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: Stratford, MR; Riley, P; Ramsden, C

• Publication status: Published
• Journal: Chemical research in toxicology
• Volume: 24
• Issue: 3
• Pages: 350-356
• Publication date: 2011-03-01
• DOI: 10.1021/tx100315n
• EISSN: 1520-5010
• ISSN: 0893-228X
• Language: English
• Keywords: Dioxins; Oxidation-Reduction; Catechols; Benzoquinones; Chromatography, High Pressure Liquid; Halogens; Monophenol Monooxygenase; Biocatalysis; Mass Spectrometry