Chloroperoxidase-catalysed oxidation of 4-chloroaniline to 4-chloronitrosobenze

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Abstract
The incubation of 4-chloroaniline with chloroperoxidase (EC 1.11.1.10) and H2O2 resulted in a rapid formation of 4-chloronitrosobenzene. This enzymic oxidation displayed a pH optimum at 4.4 with a Km of 8.1 .times. 10-4 M and catalytic-center activity of 312. The initial rate of the reaction was strongly affected by the presence of halide ions. 4-Chlorophenylhydroxylamine was even more rapidly converted into the nitroso compound. A reaction mechanism is proposed on the basis of currently accepted theory for the catalytic action of chloroperoxidase. A noteworthy aspect of this new reaction is the difference in the products previously reported for the action of classical peroxidases on anilines and the single nitroso product resulting from chloroperoxidase oxidation. [The metabolism of anilines by chloroperoxidase may serve as a model for the metabolic disposition of aniline pollutants in the environment.].