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J. Biol. Chem., Vol. 262, Issue 23, 11080-11087, 08, 1987

Semiquinone anion radicals from addition of amino acids, peptides, and proteins to quinones derived from oxidation of catechols and catecholamines. An ESR spin stabilization study

B Kalyanaraman, PI Premovic and RC Sealy

Either chemical or enzymatic oxidation of catechols or catecholamines in the presence of nucleophiles (amino acids, peptides, and proteins) leads to the production of ring-substituted o-semiquinones which have been detected by ESR spin stabilization techniques. In many cases, radicals have been completely characterized and structures assigned. Chemical considerations point to a mechanism involving addition of nucleophile to o-quinone, followed by oxidation of product to o- semiquinone. These results confirm that addition occurs in oxidizing polyhydroxy aromatic systems, probably via o-quinone, in a reaction considered to account for much of the toxicity found for catechols and catecholamines.
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