Biochemical and Biophysical Research Communications 1995-09-14

Autoxidation of 4-methylcatechol: a model for the study of the biosynthesis of copper amine oxidases quinonoid cofactor.

A C Rinaldi, M C Porcu, N Curreli, A Rescigno, A Finazzi-Agró, J Z Pedersen, A Rinaldi, E Sanjust

Index: Biochem. Biophys. Res. Commun. 214(2) , 559-67, (1995)

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Abstract

The autoxidation of 4-methylcatechol under quasi-physiological conditions, leading to 2-hydroxy-5-methyl-1,4-benzoquinone, was investigated. The effects of pH and metal ions were examined. An electrophilic attack of dioxygen to the 4-methylcatechol monoanion to form a transient peroxo species is proposed. It was concluded that such a non-enzymic conversion is likely for this model compound and for its physiological counterpart, a specific tyrosyl residue incorporated in the protein chain at the active site of copper amine oxidases.