Abstract：
:The reactions of aqueous ClO2 with tyrosine, N-acetyltyrosine, and dopa (3,4-dihydroxyphenylalanine) are investigated from pH 4 to 7. The reaction rates increase greatly with pH to give a series of oxidized products. Tyrosine and N-acetyltyrosine have similar reactivities with second-order rate constants (25.0 degrees C) for their phenoxide forms equal to 1.8x10(8) and 7.6x10(7) M-1 s-1, respectively. Both species generate phenoxyl radicals that react rapidly with a second ClO2 at the 3 position to give observable but short-lived adducts with proposed C(H)OClO bonding. The decay of these phenoxyl-ClO2 adducts also is rapid and is base-assisted to form dopaquinone (from tyrosine) and N-acetyldopaquinone (from N-acetyltyrosine) as initial products. The consumption of two ClO2 molecules corresponds to a four-electron oxidation that gives ClO2- in the first step and HOCl in the second step. The reaction between ClO2 and the deprotoned-catechol form of dopa is extremely fast (2.8x10(9) M-1 s-1). Dopa consumes two ClO2 to give dopaquinone and 2ClO2- as products. Above pH 4, dopaquinone cyclizes to give cyclodopa, which in turn is rapidly oxidized to dopachrome. A resolved first-order rate constant of 249 s-1 is evaluated for the cyclization of the basic form of dopaquinone that leads to dopachrome as a product with strong absorption bands at 305 and 485 nm.
journal_name
Chem Res Toxicoljournal_title
Chemical research in toxicologyauthors
Napolitano MJ,Green BJ,Nicoson JS,Margerum DWdoi
10.1021/tx049697isubject
Has Abstractpub_date
2005-03-01 00:00:00pages
501-8issue
3eissn
0893-228Xissn
1520-5010journal_volume
18pub_type
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