Kinetic characterisation of o-aminophenols and aromatic o-diamines as suicide substrates of tyrosinase

Biochimica Et Biophysica Acta
Jose Luis Muñoz-MuñozF García-Cánovas

Abstract

We study the suicide inactivation of tyrosinase acting on o-aminophenols and aromatic o-diamines and compare the results with those obtained for the corresponding o-diphenols. The catalytic constants follow the order aromatic o-diamines<o-aminophenols<o-diphenols, which agrees with the view that the transfer of the proton to the peroxide group of the oxy-tyrosinase form is the slowest step in the catalytic cycle. As regards the apparent inactivation constant, it remains within the same order of magnitude, although slightly lower in the case of the aromatic o-diamines and o-aminophenols than o-diphenols: o-diamines<o-aminophenols<o-diphenols. The efficiency of the second nucleophilic attack of substrate on CuA seems to be the determining factor in the bifurcation of the inactivation and catalytic pathways. This attack is more efficient in o-diamines (where it attacks a nitrogen atom) than in o-aminophenols and o-diphenols (where it attacks an oxygen atom), favouring the catalytic pathway and slowing down the inactivation pathway. The inactivation step is the slowest of the whole process. The values of r, the number of turnovers that 1mol of enzyme carries out before being inactivated, follows the order aromatic o-diamines<o-amin...Continue Reading

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Citations

Apr 3, 2013·Journal of the American Chemical Society·Takeshi MatsumotoMasako Kato
Apr 13, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Jose Luis Muñoz-MuñozFrancisco García-Cánovas
Aug 3, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sutthiduean Chunhakant, Chanya Chaicharoenpong
Feb 9, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Samaneh ZolghadriAli Akbar Saboury

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