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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.
Publication status:
Published

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Publisher copy:
10.1021/tx100315n

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Journal:
Chemical research in toxicology
Volume:
24
Issue:
3
Pages:
350-356
Publication date:
2011-03-05
DOI:
EISSN:
1520-5010
ISSN:
0893-228X
URN:
uuid:72dc28e3-d539-4729-a573-49e134676d30
Source identifiers:
132440
Local pid:
pubs:132440

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