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Xylene monooxygenase, a membrane-spanning non-heme diiron enzyme that hydroxylates hydrocarbons via a substrate radical intermediate

https://doi.org/10.1007/s00775-003-0466-3
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Outgoing claims: the papers this work cites, builds on, or argues with.

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The fundamental, versatile role of diiron enzymes in lipid metabolism
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Determination of the Carbon Kinetic Isotope Effects on Propane Hydroxylation Mediated by the Methane Monooxygenases from Methylococcus capsulatus (Bath) by Using Stable Carbon Isotopic Analysis
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Dioxygen Activation and Methane Hydroxylation by Soluble Methane Monooxygenase: A Tale of Two Irons and Three Proteins A list of abbreviations can be found in Section 7.
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Chameleon States: High-Valent Metal-Oxo Species of Cytochrome P450 and Its Ruthenium Analogue
inferredcites →https://doi.org/10.1002/1521-3773(20011001)40:19<3503::aid-anie33333503>3.0.co;2-oopenalex-snapshot
Chameleon States: High-Valent Metal–Oxo Species of Cytochrome P450 and Its Ruthenium Analogue The research in HU was sponsored by the Binational German Israeli Foundation (GIF) and by the Israeli Ministry of Science, Culture and Sport. Partial support by the US National Science Foundation…
inferredcites →https://doi.org/10.1002/anie.199207741openalex-snapshot
Enzymatic Oxidation of Methyl Groups on Aromatic Heterocycles: A Versatile Method for the Preparation of Heteroaromatic Carboxylic Acids
inferredcites →https://doi.org/10.1007/978-1-4757-2391-5openalex-snapshot
Cytochrome P450
inferredcites →https://doi.org/10.1016/0006-291x(78)91643-1openalex-snapshot
Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450. Evidence for a carbon radical intermediate
inferredcites →https://doi.org/10.1016/0041-0101(83)90286-6openalex-snapshot
Pure appl. Chem
inferredcites →https://doi.org/10.1016/s0021-9258(18)81762-8openalex-snapshot
Methane monooxygenase from Methylosinus trichosporium OB3b
inferredcites →https://doi.org/10.1016/s0021-9258(18)99684-5openalex-snapshot
Enzymatic ω-Oxidation
inferredcites →https://doi.org/10.1016/s0040-4039(00)75204-xopenalex-snapshot
Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds
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Diaklylaluminum chloride catalyzed ene reactions of aldehydes. Synthesis of ipsenol
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Methyl substituent effects on cyclopropylcarbinyl-cyclopropylcarbinyl cation rearrangements in the 2-bicyclo[4.1.0]heptyl system
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Spectroscopic studies of peroxyacetic acid reaction intermediates of cytochrome P450cam and chloroperoxidase
inferredcites →https://doi.org/10.1016/s0167-4838(00)00199-0openalex-snapshot
Mechanistic insights into C–H activation from radical clock chemistry: oxidation of substituted methylcyclopropanes catalyzed by soluble methane monooxygenase from Methylosinus trichosporium OB3b
inferredcites →https://doi.org/10.1016/s0168-6496(02)00282-9openalex-snapshot
Prevalence of alkane monooxygenase genes in Arctic and Antarctic hydrocarbon-contaminated and pristine soils
inferredcites →https://doi.org/10.1016/s0958-1669(02)00334-8openalex-snapshot
Enzyme technology: an overview
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Oxidative biotransformations using oxygenases
inferredcites →https://doi.org/10.1021/ar0001665openalex-snapshot
A View at the Millennium: the Efficiency of Enzymatic Catalysis
inferredcites →https://doi.org/10.1021/ar960058bopenalex-snapshot
Hypersensitive Radical Probes and the Mechanisms of Cytochrome P450-Catalyzed Hydroxylation Reactions
inferredcites →https://doi.org/10.1021/ar990028jopenalex-snapshot
Two-State Reactivity as a New Concept in Organometallic Chemistry
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Eight Histidine Residues Are Catalytically Essential in a Membrane-Associated Iron Enzyme, Stearoyl-CoA Desaturase, and Are Conserved in Alkane Hydroxylase and Xylene Monooxygenase
inferredcites →https://doi.org/10.1021/bi00459a005openalex-snapshot
Methane monooxygenase catalyzed oxygenation of 1,1-dimethylcyclopropane. Evidence for radical and carbocationic intermediates
inferredcites →https://doi.org/10.1021/bi00531a026openalex-snapshot
Stereochemistry and deuterium isotope effects in camphor hydroxylation by the cytochrome P450cam monooxygenase system
inferredcites →https://doi.org/10.1021/cr00036a005openalex-snapshot
Aspects of Methane Chemistry
inferredcites →https://doi.org/10.1021/cr9500489openalex-snapshot
Dioxygen Activation by Enzymes Containing Binuclear Non-Heme Iron Clusters
inferredcites →https://doi.org/10.1021/ed062p928openalex-snapshot
Key elements of the chemistry of cytochrome P-450: The oxygen rebound mechanism
inferredcites →https://doi.org/10.1021/ic00294a014openalex-snapshot
Selectivity control by axial ligand modification in manganese porphyrin-catalyzed oxidations
inferredcites →https://doi.org/10.1021/ja00015a061openalex-snapshot
Pseudomonas oleovorans monooxygenase-catalyzed asymmetric epoxidation of allyl alcohol derivatives and hydroxylation of a hypersensitive radical probe with the radical ring-opening rate exceeding the oxygen-rebound rate
inferredcites →https://doi.org/10.1021/ja00045a037openalex-snapshot
Cryptic stereospecificity of methane monooxygenase
inferredcites →https://doi.org/10.1021/ja001500vopenalex-snapshot
The Non-Heme Diiron Alkane Monooxygenase of Pseudomonas oleovorans (AlkB) Hydroxylates via a Substrate Radical Intermediate
inferredcites →https://doi.org/10.1021/ja00245a037openalex-snapshot
Timing of the radical recombination step in cytochrome P-450 catalysis with ring-strained probes
inferredcites →https://doi.org/10.1021/ja00319a044openalex-snapshot
Hydroxylation by cytochrome P-450 and metalloporphyrin models. Evidence for allylic rearrangement
inferredcites →https://doi.org/10.1021/ja00337a049openalex-snapshot
Mechanistic studies on non-heme iron monooxygenase catalysis: epoxidation, aldehyde formation and demethylation by the .omega.-hydroxylation system of Pseudomonas oleovorans
inferredcites →https://doi.org/10.1021/ja003583lopenalex-snapshot
Hydroxylation of Camphor by Reduced Oxy-Cytochrome P450cam: Mechanistic Implications of EPR and ENDOR Studies of Catalytic Intermediates in Native and Mutant Enzymes
inferredcites →https://doi.org/10.1021/ja00540a050openalex-snapshot
Hydrocarbon oxidations with oxometalloporphinates. Isolation and reactions of a (porphinato)manganese(V) complex
inferredcites →https://doi.org/10.1021/ja016376+openalex-snapshot
Intermediate Q from Soluble Methane Monooxygenase Hydroxylates the Mechanistic Substrate Probe Norcarane: Evidence for a Stepwise Reaction
inferredcites →https://doi.org/10.1021/ja017858oopenalex-snapshot
Evaluation of Norcarane as a Probe for Radicals in Cytochome P450- and Soluble Methane Monooxygenase-Catalyzed Hydroxylation Reactions
inferredcites →https://doi.org/10.1021/ja025608hopenalex-snapshot
Revisiting the Mechanism of P450 Enzymes with the Radical Clocks Norcarane and Spiro[2,5]octane
inferredcites →https://doi.org/10.1021/ja953407qopenalex-snapshot
A Concerted Mechanism for Ethane Hydroxylation by the Particulate Methane Monooxygenase from Methylococcus capsulatus (Bath)
inferredcites →https://doi.org/10.1021/ja963971gopenalex-snapshot
Tritiated Chiral Alkanes as Substrates for Soluble Methane Monooxygenase fromMethylococcus capsulatus(Bath): Probes for the Mechanism of Hydroxylation
inferredcites →https://doi.org/10.1021/ja971049gopenalex-snapshot
Regio- and Stereoselectivity of Particulate Methane Monooxygenase from Methylococcus capsulatus (Bath)
inferredcites →https://doi.org/10.1021/ja981157iopenalex-snapshot
Hypersensitive Mechanistic Probe Studies of Cytochrome P450-Catalyzed Hydroxylation Reactions. Implications for the Cationic Pathway
inferredcites →https://doi.org/10.1021/ja993259uopenalex-snapshot
Cationic Species Can Be Produced in Soluble Methane Monooxygenase-Catalyzed Hydroxylation Reactions; Radical Intermediates Are Not Formed
inferredcites →https://doi.org/10.1021/ja994106+openalex-snapshot
Cytochrome P450-Catalyzed Hydroxylation of Mechanistic Probes that Distinguish between Radicals and Cations. Evidence for Cationic but Not for Radical Intermediates
inferredcites →https://doi.org/10.1021/jo00025a007openalex-snapshot
A comparison of (chloromethyl)- and (iodomethyl)zinc cyclopropanation reagents
inferredcites →https://doi.org/10.1021/jo01265a089openalex-snapshot
Synthesis of homoallylic alcohols
inferredcites →https://doi.org/10.1021/jo01338a002openalex-snapshot
Methyl substituent effects upon the chemistry of 2-bicyclo[4.1.0]heptyl 3,5-dinitrobenzoates
inferredcites →https://doi.org/10.1038/366537a0openalex-snapshot
Crystal structure of a bacterial non-haem iron hydroxylase that catalyses the biological oxidation of methane
inferredcites →https://doi.org/10.1038/nbt0486-321openalex-snapshot
New Route to Bacterial Production of Indigo
inferredcites →https://doi.org/10.1038/sj.jim.2900475openalex-snapshot
Aromatic hydrocarbon degradation by Sphingomonas yanoikuyae B1
inferredcites →https://doi.org/10.1038/sj.jim.2900724openalex-snapshot
Functional analysis of genes involved in biphenyl, naphthalene, phenanthrene, and m -xylene degradation by Sphingomonas yanoikuyae B1
inferredcites →https://doi.org/10.1039/b105571mopenalex-snapshot
Stereospecific oxidation by Compound I of Cytochrome P450 does not proceed in a concerted synchronous manner
inferredcites →https://doi.org/10.1042/bj20020823openalex-snapshot
The membrane-associated form of methane mono-oxygenase from Methylococcus capsulatus (Bath) is a copper/iron protein
inferredcites →https://doi.org/10.1046/j.1462-2920.1999.00037.xopenalex-snapshot
Molecular screening for alkane hydroxylase genes in Gram‐negative and Gram‐positive strains
inferredcites →https://doi.org/10.1073/pnas.0830019100openalex-snapshot
The bioinorganic chemistry of iron in oxygenases and supramolecular assemblies
inferredcites →https://doi.org/10.1073/pnas.94.7.2981openalex-snapshot
Mössbauer studies of alkane ω-hydroxylase: Evidence for a diiron cluster in an integral-membrane enzyme
inferredcites →https://doi.org/10.1074/jbc.274.16.10771openalex-snapshot
Oxidation of Ultrafast Radical Clock Substrate Probes by the Soluble Methane Monooxygenase from Methylococcus capsulatus(Bath)
inferredcites →https://doi.org/10.1074/jbc.275.14.10085openalex-snapshot
Xylene Monooxygenase Catalyzes the Multistep Oxygenation of Toluene and Pseudocumene to Corresponding Alcohols, Aldehydes, and Acids in Escherichia coli JM101
inferredcites →https://doi.org/10.1074/jbc.c100745200openalex-snapshot
Kinetic Characterization of Compound I Formation in the Thermostable Cytochrome P450 CYP119
inferredcites →https://doi.org/10.1099/00221287-43-2-159openalex-snapshot
The Aerobic Pseudomonads a Taxonomic Study
inferredcites →https://doi.org/10.1111/j.1574-6941.2002.tb00975.xopenalex-snapshot
Prevalence of alkane monooxygenase genes in Arctic and Antarctic hydrocarbon-contaminated and pristine soils1
inferredcites →https://doi.org/10.1126/science.3358128openalex-snapshot
Probing Structure-Function Relations in Heme-Containing Oxygenases and Peroxidases
inferredcites →https://doi.org/10.1128/aem.65.6.2324-2332.1999openalex-snapshot
An Alkane-Responsive Expression System for the Production of Fine Chemicals
inferredcites →https://doi.org/10.1128/jb.173.5.1690-1695.1991openalex-snapshot
Primary structure of xylene monooxygenase: similarities to and differences from the alkane hydroxylation system
inferredcites →https://doi.org/10.1128/mr.54.3.305-315.1990openalex-snapshot
Microbial degradation of hydrocarbons in the environment
inferredcites →https://doi.org/10.1146/annurev.bi.49.070180.001531openalex-snapshot
Oxygen Activation by Cytochrome P-4501
inferredcites →https://doi.org/10.1351/pac198759060759openalex-snapshot
Cytochrome P-450 and synthetic models

What points at this work

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

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Directed evolution of an integral membrane monooxygenase unlocks its full potential
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Remarkable Aliphatic Hydroxylation by the Diiron Enzyme Toluene 4-Monooxygenase in Reactions with Radical or Cation Diagnostic Probes Norcarane, 1,1-Dimethylcyclopropane, and 1,1-Diethylcyclopropane
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Benchmarking the Reactivity of Caged Iron(IV)-Oxo Sites within Metal–Organic Frameworks
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Desaturase Reactions Complicate the Use of Norcarane as a Mechanistic Probe. Unraveling the Mixture of Twenty-Plus Products Formed in Enzyme-Catalyzed Oxidations of Norcarane
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