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Mechanistic aspects of the tyrosinase oxidation of hydroquinone

Abstract

Contradictory reports on the behaviour of hydroquinone as a tyrosinase substrate are reconciled in terms of the ability of the initially formed ortho-quinone to tautomerise to the thermodynamically more stable para-quinone isomer. Oxidation of phenols by native tyrosinase requires activation by in situ formation of a catechol formed via an enzyme generated ortho-quinone. In the special case of hydroquinone, catechol formation is precluded by rapid tautomerisation of the ortho-quinone precursor to catechol formation.

Acceptance Date Apr 6, 2014
Publication Date Jun 1, 2014
Journal Bioorganic & Medicinal Chemistry Letters
Print ISSN 0960-894X
Publisher Elsevier
Pages 2463 - 2464
DOI https://doi.org/10.1016/j.bmcl.2014.04.009
Keywords Hydroquinone; Tyrosinase; ortho-Quinones; para-Quinones; Tautomerism
Publisher URL https://www.sciencedirect.com/science/article/pii/S0960894X1400345X?via%3Dihub

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