Catalytic oxidation of acetaminophen by tyrosinase in the presence of L-proline: a kinetic study.

Abstract:

:A kinetic study of acetaminophen oxidation by tyrosinase in the presence of a physiological nucleophilic agent such as the amino acid L-proline is performed in the present paper. The o-quinone product of the catalytic activity, 4-acetamido-o-benzoquinone, becomes unstable through the chemical addition of L-proline, in competition with the nucleophilic addition of hydroxide ion from water. In both cases, the catechol intermediate, 3(')-hydroxyacetaminophen, is generated, as can be demonstrated by liquid chromatography. When the effect of the presence of the nucleophilic agent on the time course of the enzymatic reaction was kinetically analyzed, it was seen to decrease the duration of the lag period and increase the steady-state rate. Rate constants for the reaction of 4-acetamido-o-benzoquinone with water and L-proline were also determined. The results obtained in this paper open a new possibility to acetaminophen toxicity, that has been attributed hitherto to its corresponding p-quinone, N-acetyl-p-benzoquinone imine.

journal_name

Arch Biochem Biophys

authors

Valero E,Varón R,García-Carmona F

doi

10.1016/s0003-9861(03)00288-1

subject

Has Abstract

pub_date

2003-08-15 00:00:00

pages

218-26

issue

2

eissn

0003-9861

issn

1096-0384

pii

S0003986103002881

journal_volume

416

pub_type

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