Aromatic methyl group migration and hydroxylation of p-toluidine by iron-thiol and hemin-thiol systems as a model of cytochrome P-450.

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The aromatic methyl group migration and hydroxylation of p-toluidine by several Fe (II)-thiol compound and hemin-thiol compound systems were investigated as a model of cytochrome P-450 of liver microsomes. In these systems, 4-hydroxy-m-toluidine, 3-hydroxy-p-toluidine and 2-hydroxy-p-toluidine were formed as the main products of the reaction. The yield of methyl group migration and hydroxylation were dependent on the type of thiol compounds, chemical form of iron (Fe (II) or hemin), pH of the reaction mixture, reaction periods as well as on the concentration of the substrates or the thiol compounds. These results on the methyl group migration of p-toluidine suggest that the Fe (II)-thiol and hemin-thiol systems can be regarded as a good chemical model for the study of the function and structure of cytochrome P-450.

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