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. 2013 May 10;52(20):5398-401.
doi: 10.1002/anie.201301249. Epub 2013 Apr 22.

Catalytic phenol hydroxylation with dioxygen: extension of the tyrosinase mechanism beyond the protein matrix

Alexander Hoffmann  1 , Cooper Citek, Stephan Binder, Arne Goos, Michael Rübhausen, Oliver Troeppner, Ivana Ivanović-Burmazović, Erik C Wasinger, T Daniel P Stack, Sonja Herres-Pawlis
Affiliations

Catalytic phenol hydroxylation with dioxygen: extension of the tyrosinase mechanism beyond the protein matrix

Alexander Hoffmann et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Figure 1
Figure 1
A) Preparation of the side-on peroxide species 1. B) Absorption spectra of 1; (inset) TD-DFT predicted optical spectrum of 1. C) Resonance Raman spectra of 1 in acetone with 412 nm excitation (red: 16O2, black: 18O2, asterisks (*): solvent peaks); (inset) isotopic shift of 750 cm−1 feature.
Figure 2
Figure 2
Reactivity at −78°C in CH2Cl2. Left: Substrate-binding kinetics of the stoichiometric hydroxylation reaction with 4-fluorophenolate. Right: Hammett plot for the stoichiometric hydroxylation reaction with 1 – 20 equiv of various p-substituted phenolates.
Figure 3
Figure 3
Proposed catalytic mechanism of phenol oxidation by 1 in the presence of triethylamine.
See this image and copyright information in PMC

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