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Catalytic Phenol Hydroxylation with Dioxygen: Extension of the Tyrosinase Mechanism beyond the Protein Matrix

https://doi.org/10.1002/anie.201301249
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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

inferredcites →https://doi.org/10.1002/(sici)1521-3765(20000204)6:3<519::aid-chem519>3.0.co;2-iopenalex-snapshot
Reversible Dioxygen Binding and Phenol Oxygenation in a Tyrosinase Model System
inferredcites →https://doi.org/10.1002/ange.201000973openalex-snapshot
Das erste katalytische Tyrosinasemodell basierend auf einem einkernigen Kupfer(I)‐Komplex: Kinetik und Mechanismus
inferredcites →https://doi.org/10.1002/anie.201000973openalex-snapshot
The First Catalytic Tyrosinase Model System Based on a Mononuclear Copper(I) Complex: Kinetics and Mechanism
inferredcites →https://doi.org/10.1002/chin.200741276openalex-snapshot
Monooxygenase Activity of Type 3 Copper Proteins
inferredcites →https://doi.org/10.1016/j.bbrc.2012.06.074openalex-snapshot
Hydroxylation of p-substituted phenols by tyrosinase: Further insight into the mechanism of tyrosinase activity
inferredcites →https://doi.org/10.1016/j.tetlet.2005.03.060openalex-snapshot
An expedient one-pot entry to catecholestrogens and other catechol compounds via IBX-mediated phenolic oxygenation
inferredcites →https://doi.org/10.1016/j.tetlet.2005.03.082openalex-snapshot
One-pot synthesis of substituted catechols from the corresponding phenols
inferredcites →https://doi.org/10.1016/s0898-8838(05)58004-8openalex-snapshot
Ligand Influences in Copper-Dioxygen Complex-Formation and Substrate Oxidations
inferredcites →https://doi.org/10.1016/s0968-0896(03)00063-4openalex-snapshot
Catechols from abietic acid
inferredcites →https://doi.org/10.1016/s1367-5931(99)00080-0openalex-snapshot
Biomimetic modeling of copper oxidase reactivity
inferredcites →https://doi.org/10.1021/ar1000956openalex-snapshot
How to Conceptualize Catalytic Cycles? The Energetic Span Model
inferredcites →https://doi.org/10.1021/ar50115a006openalex-snapshot
Synthetic models for the oxygen-binding hemoproteins
inferredcites →https://doi.org/10.1021/ar6000395openalex-snapshot
Monooxygenase Activity of Type 3 Copper Proteins
inferredcites →https://doi.org/10.1021/cr00027a006openalex-snapshot
Synthetic Heme-Dioxygen Complexes
inferredcites →https://doi.org/10.1021/cr020632zopenalex-snapshot
Structure and Spectroscopy of Copper−Dioxygen Complexes
inferredcites →https://doi.org/10.1021/cr020633ropenalex-snapshot
Reactivity of Dioxygen−Copper Systems
inferredcites →https://doi.org/10.1021/cr950046oopenalex-snapshot
Multicopper Oxidases and Oxygenases
inferredcites →https://doi.org/10.1021/ja00077a027openalex-snapshot
Chemistry and structural studies on the dioxygen-binding copper-1,2-dimethylimidazole system
inferredcites →https://doi.org/10.1021/ja00110a004openalex-snapshot
A Model Compound of the Novel Cofactor Tryptophan Tryptophylquinone of Bacterial Methylamine Dehydrogenases. Synthesis and Physicochemical Properties
inferredcites →https://doi.org/10.1021/ja00536a044openalex-snapshot
Chemical and spectroscopic comparison of the binuclear copper active site of mollusc and arthropod hemocyanins
inferredcites →https://doi.org/10.1021/ja015702iopenalex-snapshot
Oxygenation of Phenols to Catechols by A (μ-η2:η2-Peroxo)dicopper(II) Complex: Mechanistic Insight into the Phenolase Activity of Tyrosinase
inferredcites →https://doi.org/10.1021/ja026905popenalex-snapshot
A Stabilized μ-η2:η2 Peroxodicopper(II) Complex with a Secondary Diamine Ligand and Its Tyrosinase-like Reactivity
inferredcites →https://doi.org/10.1021/ja036425dopenalex-snapshot
Kinetic Evaluation of Phenolase Activity of Tyrosinase Using Simplified Catalytic Reaction System
inferredcites →https://doi.org/10.1021/ja0544298openalex-snapshot
Hydroxylation of Phenolic Compounds by a Peroxodicopper(II) Complex: Further Insight into the Mechanism of Tyrosinase
inferredcites →https://doi.org/10.1021/ja208572vopenalex-snapshot
Synthesis of Catechols from Phenols via Pd-Catalyzed Silanol-Directed C–H Oxygenation
inferredcites →https://doi.org/10.1021/ja807809xopenalex-snapshot
Phenolate Hydroxylation in a Bis(μ-oxo)dicopper(III) Complex: Lessons from the Guanidine/Amine Series
inferredcites →https://doi.org/10.1021/ja992017ropenalex-snapshot
Re-engineering Enzyme-Model Active Sites: Reversible Binding of Dioxygen at Ambient Conditions by a Bioinspired Copper Complex
inferredcites →https://doi.org/10.1021/ja992295qopenalex-snapshot
Crystal Structure and Reversible O2-Binding of a Room Temperature Stable μ-η2:η2-Peroxodicopper(II) Complex of a Sterically Hindered Hexapyridine Dinucleating Ligand
inferredcites →https://doi.org/10.1021/jf301238qopenalex-snapshot
Action of Tyrosinase on Ortho-Substituted Phenols: Possible Influence on Browning and Melanogenesis
inferredcites →https://doi.org/10.1038/nature07371openalex-snapshot
Biologically inspired oxidation catalysis
inferredcites →https://doi.org/10.1038/nchem.1284openalex-snapshot
Self-assembly of the oxy-tyrosinase core and the fundamental components of phenolic hydroxylation
inferredcites →https://doi.org/10.1039/c0cs00202jopenalex-snapshot
Copper–O2 reactivity of tyrosinase models towards external monophenolic substrates: molecular mechanism and comparison with the enzyme
inferredcites →https://doi.org/10.1039/c39900001752openalex-snapshot
Binuclear copper complex model of tyrosinase
inferredcites →https://doi.org/10.1039/c39910001611openalex-snapshot
A tyrosinase model system. Phenol ortho-hydroxylation by a binuclear three-coordinate copper(I) complex and dioxygen
inferredcites →https://doi.org/10.1042/bj0340051openalex-snapshot
The inactivation of oestrone
inferredcites →https://doi.org/10.1063/1.1558471openalex-snapshot
Natural transition orbitals
inferredcites →https://doi.org/10.1074/jbc.m509785200openalex-snapshot
Crystallographic Evidence That the Dinuclear Copper Center of Tyrosinase Is Flexible during Catalysis
inferredcites →https://doi.org/10.1111/j.1600-0749.1998.tb00707.xopenalex-snapshot
N‐Acetyl‐L‐Tyrosine (NAT) as a Substrate for Mushroom Tyrosinase

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

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inferred← citeshttps://doi.org/10.1021/acs.inorgchem.9b00901openalex-snapshot
Directed Hydroxylation of sp2 and sp3 C–H Bonds Using Stoichiometric Amounts of Cu and H2O2
inferred← citeshttps://doi.org/10.1021/acs.joc.1c00656openalex-snapshot
Aerobic Copper-Catalyzed Intramolecular Cascade Oxidative Isomerization/[4+4] Cyclization of 2,2′-Disubstituted Stilbenes
inferred← citeshttps://doi.org/10.1021/acs.joc.9b01573openalex-snapshot
Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1H-pyrroles: Synthesis of Benzo/Furo/Thieno[e]-Fused 1H-Indol-7-oles and Their Transformations
inferred← citeshttps://doi.org/10.1021/acs.organomet.3c00014openalex-snapshot
Copper Complexes Supported by Iminotriazole Ligands: Effective Catalysts for the Monooxygenation of Phenols
inferred← citeshttps://doi.org/10.1021/acs.orglett.1c00071openalex-snapshot
Benzene-Free Synthesis of Multisubstituted Catechol via Oxidative Dearomatic Reorganization
inferred← citeshttps://doi.org/10.1021/acscatal.1c06011openalex-snapshot
Engineering P450 Monooxygenases for Highly Regioselective and Active p -Hydroxylation of m -Alkylphenols
inferred← citeshttps://doi.org/10.1021/acsnano.0c09563openalex-snapshot
X-ray-Based Techniques to Study the Nano–Bio Interface
inferred← citeshttps://doi.org/10.1021/acsomega.9b01945openalex-snapshot
Polymer-Coated Mesoporous Carbon as Enzyme Platform for Oxidation of Bisphenol A in Organic Solvents
inferred← citeshttps://doi.org/10.1021/ja501789xopenalex-snapshot
Controlling the Catalytic Aerobic Oxidation of Phenols
inferred← citeshttps://doi.org/10.1021/jacs.2c08140openalex-snapshot
Peroxide-Selective Reduction of O 2 at Redox-Inactive Rare-Earth(III) Triflates Generates an Ambiphilic Peroxide
inferred← citeshttps://doi.org/10.1021/jacs.3c07450openalex-snapshot
Experimental Evidence and Mechanistic Description of the Phenolic H-Transfer to the Cu 2 O 2 Active Site of oxy-Tyrosinase
inferred← citeshttps://doi.org/10.1021/jacs.4c06243openalex-snapshot
Dioxygenase Chemistry in Nucleophilic Aldehyde Deformylations Utilizing Dicopper O 2 -Derived Peroxide Complexes
inferred← citeshttps://doi.org/10.1021/jacs.5b08347openalex-snapshot
Factors That Control C–C Cleavage versus C–H Bond Hydroxylation in Copper-Catalyzed Oxidations of Ketones with O2
inferred← citeshttps://doi.org/10.1021/om501139fopenalex-snapshot
Synthesis of Multinuclear Copper Complexes Bridged by Diquinolylamidinates and Their Application to Copper-Catalyzed Coupling of Terminal Alkynes and Aryl, Allyl, and Benzyl Halides
inferred← citeshttps://doi.org/10.1039/c3cc47888bopenalex-snapshot
New catalytic model systems of tyrosinase: fine tuning of the reactivity with pyrazole-based N-donor ligands
inferred← citeshttps://doi.org/10.1039/c4dt03010aopenalex-snapshot
Monooxygenation of an appended phenol in a model system of tyrosinase: implications on the enzymatic reaction mechanism
inferred← citeshttps://doi.org/10.1039/c5cc02806jopenalex-snapshot
Controlled nitrene transfer from a tyrosinase-like arylnitroso–copper complex
inferred← citeshttps://doi.org/10.1039/c5dt00822kopenalex-snapshot
Catalytic aerobic oxidation of phenols to ortho-quinones with air-stable copper precatalysts
inferred← citeshttps://doi.org/10.1039/c5sc02395eopenalex-snapshot
A bio-inspired synthesis of oxindoles by catalytic aerobic dual C–H functionalization of phenols
inferred← citeshttps://doi.org/10.1039/c6ob01183gopenalex-snapshot
Copper-catalyzed divergent oxidative pathways of 2-naphthol derivatives: ortho-naphthoquinones versus 2-BINOLs
inferred← citeshttps://doi.org/10.1039/c6sc04820jopenalex-snapshot
Acid/base triggered interconversion of μ-η 2 :η 2 -peroxido and bis(μ-oxido) dicopper intermediates capped by proton-responsive ligands
inferred← citeshttps://doi.org/10.1039/c7cp04686copenalex-snapshot
Relativistic effects at the Cu 2 O 2 core – a density functional theory study
inferred← citeshttps://doi.org/10.1039/c7dt00147aopenalex-snapshot
A dinuclear biomimetic Cu complex derived from l -histidine: synthesis and stereoselective oxidations
inferred← citeshttps://doi.org/10.1039/c7ra06917kopenalex-snapshot
Ferrocene particles incorporated into Zr-based metal–organic frameworks for selective phenol hydroxylation to dihydroxybenzenes
inferred← citeshttps://doi.org/10.1039/c8dt03992eopenalex-snapshot
Multiple coordination modes of a new ditopic bis(pyrazolyl)methane-based ligand
inferred← citeshttps://doi.org/10.1039/c9cc00437hopenalex-snapshot
A bio-inspired imidazole-functionalised copper cage complex
inferred← citeshttps://doi.org/10.1039/c9dt00516aopenalex-snapshot
Dual oxidase/oxygenase reactivity and resonance Raman spectra of {Cu 3 O 2 } moiety with perfluoro- t -butoxide ligands
inferred← citeshttps://doi.org/10.1039/d1dt00832copenalex-snapshot
A new generation of terminal copper nitrenes and their application in aromatic C–H amination reactions
inferred← citeshttps://doi.org/10.1039/d4dt02872dopenalex-snapshot
Selective hydroxylation of benzene to phenol via Cu II (μ-O˙)Cu II intermediate using a nonsymmetric dicopper catalyst
inferred← citeshttps://doi.org/10.1039/d5cy00956aopenalex-snapshot
sp 3 C–H alkylation of fluorenes catalyzed by o -phenylene-bridged noninnocent bis-azopyridyl complexes of copper
inferred← citeshttps://doi.org/10.1055/s-0037-1610297openalex-snapshot
Advances in Catalytic Aerobic Oxidations by Activation of Dioxygen-Monooxygenase Enzymes and Biomimetics
inferred← citeshttps://doi.org/10.1055/sos-sd-218-00197openalex-snapshot
2.10 C—O Bond Formation by Arene C—H Activation via Biomimetic and Organocatalytic Oxidation
inferred← citeshttps://doi.org/10.1055/sos-sd-225-00304openalex-snapshot
9 Catalytic Aerobic Oxidation of Phenols
inferred← citeshttps://doi.org/10.1080/00958972.2015.1074191openalex-snapshot
Catalytic oxygenation of various monophenols by copper(I) complexes with bis(pyrazolyl)methane ligands: differences in reactivity
inferred← citeshttps://doi.org/10.1109/iwsg.2014.18openalex-snapshot
Expansion of Quantum Chemical Metadata for Workflows in the MoSGrid Science Gateway
inferred← citeshttps://doi.org/10.1177/19322968221123083openalex-snapshot
Electrooxidation of Phenol on Polyelectrolyte Modified Carbon Electrodes for Use in Insulin Pump Infusion Sets
inferred← citeshttps://doi.org/10.1515/znb-2021-0140openalex-snapshot
Chiral bis(pyrazolyl)methane copper(I) complexes and their application in nitrene transfer reactions
inferred← citeshttps://doi.org/10.3390/inorganics6040114openalex-snapshot
Fluorescent Bis(guanidine) Copper Complexes as Precursors for Hydroxylation Catalysis
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