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- W2000773809 abstract "The mechanism of o-semiquinone production was examined in the tyrosinase and peroxidase catalyzed oxidations of a series of catecholic compounds using the electron spin resonance (ESR) spin-stabilization approach and in the presence of 3-methyl-2-benzothiazolinone hydrazone (MBTH). In the tyrosinase process, the nonenzymatic o-semiquinone formation by inverse disproportion mechanism was clearly confirmed. Mechanistic and kinetic studies of o-semiquinone and o-quinone formation by mushroom tyrosinase were carried out by ESR spin stabilization and optical spectroscopy. Two different types of cyclizable catecholic substrates (l-dopa and dopamine 3,4-dihydroxyphenylacetic acid and 3-(3,4-dihydroxyphenyl)propionic acid) together with an uncyclizable substrate (3,4-dihydroxybenzoic acid) were examined. The reactive quinones were monitored by measuring the apparent initial rates of the o-quinone-MBTH adducts. The transient behaviour of the o-semiquinone was studied by determining the pseudo first-order formation constants (k values in the range 0.226–0.035 s−1), the relative second-order decay kinetic constants (k = 3.3·102 M−1 s−1 for dopamine o-semiquinone) and the maximum concentrations of the o-semiquinone complexes formed in situ with Mg2+ ions. The o-semiquinone formation constants are not directly correlated with their maximum concentrations; in fact, the o-semiquinone maximum concentration of the uncyclizable substrate is comparable with that derived from l-dopa. Furthermore, the secondary semiquinone formation is slow and not competitive with the primary semiquinone generation. Then, in our model the limiting factor for the o-semiquinone formation, is not simply the substrate ability to cyclize, and, therefore, the potential toxicity of the secondary semiquinone is questionable." @default.
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- W2000773809 date "1997-10-01" @default.
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- W2000773809 title "Tyrosinase-catecholic substrates in Vitro model: kinetic studies on the o-quinone/o-semiquinone radical formation" @default.
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- W2000773809 doi "https://doi.org/10.1016/s0162-0134(97)81617-0" @default.
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