19641-91-9Relevant academic research and scientific papers
Regioselective Oxidation of Phenols Catalyzed by Polyphenol Oxidase in Chloroform
Kazandjian, Rafi Z.,Klibanov, Alexander M.
, p. 5448 - 5450 (1985)
Mushroom polyphenol oxidase can catalyze the oxidation of a number of phenols to o-quinones in chloroform.While in water the enzymatic oxidation results in negligible yields due to rapid inactivation of the enzyme and spontaneous polymerization of the quinones, in chloroform a quantitative conversion has been achieved; the quinones produced have been nonenzymatically reduced to catechols, thereby affording a net regioselective polyphenol oxidase catalyzed hydroxylation of phenols.
Catalytic phenol hydroxylation with dioxygen: Extension of the tyrosinase mechanism beyond the protein matrix
Hoffmann, Alexander,Citek, Cooper,Binder, Stephan,Goos, Arne,Ruebhausen, Michael,Troeppner, Oliver,Ivanovic-Burmazovic, Ivana,Wasinger, Erik C.,Stack, T. Daniel P.,Herres-Pawlis, Sonja
supporting information, p. 5398 - 5401 (2013/06/27)
A new catalyst (see structure) hydroxylates phenols with O2 via a stable side-on peroxide complex, which is similar to the active site of tyrosinase in terms of the ligand environment and its spectroscopic properties. The catalytic oxidation of phenols to quinones proceeds at room temperature in the presence of NEt3 and even non-native substrates can be oxidized catalytically. The reaction mechanism is analogous to that of the enzyme-catalyzed reaction. Copyright
