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cytoplasmic methane monooxygenase
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methane hydroxylase
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methane mono-oxygenase
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methane monooxygenase
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methane monooxygenase hydroxylase
oxygenase, methane mono-
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particulate methane monooxygenase
soluble methane monooxygenase
soluble methane monooxygenase hydroxylase
chcA

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methane monooxygenase hydroxylase

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methane monooxygenase hydroxylase
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MmMmoC

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MMO

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MMO Bath

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MMOB

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cofactor-free, monomeric component of sMMO, has regulatory role in catalysis
MmoC

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MMOH

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MMOH
diiron(II) center of the hydroxylase component of soluble methane monooxygenase
MMOH
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hydroxylase component of sMMO, contains a binuclear nonheme iron active site that is essential for O2 activation and subsequent methane oxidation
MMOR

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reductase component of sMMO, contains a FAD cofactor and a [2Fe-2S] cluster, is responsible for transferring the reducing equivalents from NAD(P)H to MMOH
particulate methane monooxygenase

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particulate methane monooxygenase
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particulate methane monooxygenase
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particulate methane monooxygenase
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particulate methane monooxygenase
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particulate methane monooxygenase
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particulate methane monooxygenase
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particulate methane monooxygenase
methylotrophic bacterium
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pMMO

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pMMO
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particulate, membrane-bound enzyme form
pMMO
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particulate, membrane-bound enzyme form
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pMMO
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particulate, membrane-bound enzyme form
pMMO
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particulate, membrane-bound enzyme form
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pMMO
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particulate, membrane-bound enzyme form
pMMO
methylotrophic bacterium
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sMMO

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sMMO
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soluble, cytoplasmic enzyme form
sMMO
the enzyme contains three protein components, a 251 kDa hydroxylase (MMOH), a 38.6 kDa reductase (MMOR), and a 15.9 kDa regulatory protein (MMOB) required to couple electron consumption with substrate hydroxylation at the catalytic diiron center of MMOH
sMMO
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soluble, cytoplasmic enzyme form
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sMMO
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multicomponent enzyme
sMMO
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soluble, cytoplasmic enzyme form
sMMO
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soluble, cytoplasmic enzyme form
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sMMO
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soluble, cytoplasmic enzyme form
soluble methane monooxygenase

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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase
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soluble methane monooxygenase hydroxylase

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soluble methane monooxygenase hydroxylase
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soluble methane monooxygenase hydroxylase
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soluble methane monooxygenase hydroxylase
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O

mechanism
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
mechanism
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
mechanism
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
structural model for component protein B of sMMO
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
kinetic model of protein component interaction
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
modeling of interaction between the different protein components of sMMO
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
distribution of electrons in intermolecular electron-transfer intermediates, isomerization of the initial ternary complex is required for maximal electron-transfer rates
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction cycle, via formation of the hydroperoxo intermediate compound P and the key reaction cycle intermediate compound Q, overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism and regulation, catalytic cycle of sMMO, the enzyme complex causes quantum tunneling to dominate in CH bond cleavage reaction for methane, selectively increasing the rate for this substrate, mechanism of C-H bond cleavage, overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism via carboxylate-bridged diiron center and dioxygen, a di(my-oxo)diiron(IV) intermediate termed Q is responsible for the catalytic activity with hydrocarbons, the peroxodiiron(III) intermediate precedes Q formation in the catalytic cycle, which consists of four principal steps, overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism, spin states analysis of polynuclear metal clusters, a dinuclear oxygen-bridged iron(IV) model for the intermediate Q of the hydroxylase component of methane monooxygenase by means of spin-unrestricted KohnSham density functional theory, overview
methylotrophic bacterium
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism, substrate radical intermediates in the reaction of soluble methane monooxygenase, the reaction involves the conversion of the enzyme hydroxylase component, MMOH, diiron cluster to a strongly oxidizing bis-l-oxo-Fe(IV)2 species termed compound Q, that is capable of the fissure of stable CH bonds in methane and many other hydrocarbons
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
the soluble enzyme utilizes a carboxylate-bridged diiron center and dioxygen, a di(my-oxo)diiron(IV) intermediate termed Q is responsible for the catalytic activity with hydrocarbons, the peroxodiiron(III) intermediate precedes Q formation in the catalytic cycle
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
via diiron(IV) reaction intermediate Q, reaction mechanism of the soluble enzyme with different substrates, overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
catalyzes the oxidation of methane through the activation of O2 at a nonheme biferrous center in the hydroxylase component MMOH
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism and reaction cycle of enzyme sMMO, via O2 activation intermediates, detailed overview
methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism of enzyme sMMO. During methane oxidation, first, the regulatory protein docks at the alpha2beta2 interface of alpha2beta2gamma2 of hydroxylase and therefore triggering a conformational change in the alpha-subunit. Subsequently, the hydroxylase acts as a proton carrier allowing oxygen and methane interface with the di-iron center, overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism with transition states, MMOHred to MMOHox transitions for open cores of MMOHQ, detailed overview. The reactivity of the Fe(IV)=O unit is modulated by the ligand to the second iron
methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism and reaction cycle of enzyme sMMO, via O2 activation intermediates, detailed overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism of enzyme sMMO. During methane oxidation, first, the regulatory protein docks at the alpha2beta2 interface of alpha2beta2gamma2 of hydroxylase and therefore triggering a conformational change in the alpha-subunit. Subsequently, the hydroxylase acts as a proton carrier allowing oxygen and methane interface with the di-iron center, overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
via diiron(IV) reaction intermediate Q, reaction mechanism of the soluble enzyme with different substrates, overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism via carboxylate-bridged diiron center and dioxygen, a di(my-oxo)diiron(IV) intermediate termed Q is responsible for the catalytic activity with hydrocarbons, the peroxodiiron(III) intermediate precedes Q formation in the catalytic cycle, which consists of four principal steps, overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
distribution of electrons in intermolecular electron-transfer intermediates, isomerization of the initial ternary complex is required for maximal electron-transfer rates
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
the soluble enzyme utilizes a carboxylate-bridged diiron center and dioxygen, a di(my-oxo)diiron(IV) intermediate termed Q is responsible for the catalytic activity with hydrocarbons, the peroxodiiron(III) intermediate precedes Q formation in the catalytic cycle
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
mechanism
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
modeling of interaction between the different protein components of sMMO
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
structural model for component protein B of sMMO
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
reaction mechanism and reaction cycle of enzyme sMMO, via O2 activation intermediates, detailed overview
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methane + NAD(P)H + H+ + O2 = methanol + NAD(P)+ + H2O
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1,1,2,2-tetramethylcyclopropane + NADH + O2
?
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?
1-butene + NAD(P)H + O2
1,2-epoxybutane + NAD(P)+ + H2O
2,3-dimethylpentane + NAD(P)H + O2
3,4-dimethylpentan-2-ol + NAD(P)+ + H2O
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?
2-methylpropane + NAD(P)H + O2
2-methylpropan-2-ol + 2-methylpropan-1-ol + NAD(P)+ + H2O
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?
adamantane + NAD(P)H + O2
1-adamantanol + 2-adamantanol + NAD(P)+ + H2O
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?
ammonia + NAD(P)H + O2
hydroxylamine + NAD(P)+ + H2O
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?
ammonia + NADH + H+ + O2
?
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?
benzene + NAD(P)H + H+ + O2
phenol + hydroquinone + NAD(P)+ + H2O
benzene + NAD(P)H + H+ + O2
phenol + NAD(P)+ + H2O
benzene + NADH + H+ + O2
?
beta-pinene + NAD(P)H + O2
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-methanol + beta-pinene oxide + NAD(P)+ + H2O
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?
biphenyl + NAD(P)H + H+ + O2
2-hydroxybiphenyl + 4-hydroxybiphenyl + NAD(P)+ + H2O
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?
bromobenzene + NAD(P)H + O2
bromophenol + NAD(P)+ + H2O
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sMMO
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?
bromomethane + NAD(P)H + O2
?
bromomethane + NADH + H+ + O2
?
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?
butane + NAD(P)H + O2
1-butanol + 2-butanol + NAD(P)+ + H2O
butylene + NAD(P)H + O2
butylene oxide + NAD(P)+ + H2O
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sMMO
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?
carbon monoxide + NADH + H+ + O2
?
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?
chlorobenzene + NAD(P)H + O2
chlorophenol + NAD(P)+ + H2O
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sMMO
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?
chloromethane + NAD(P)H + O2
formaldehyde + NAD(P)+ + H2O + ?
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?
chloromethane + NADH + H+ + O2
?
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?
chloronaphthalene + NAD(P)H + O2
chloronaphthol + NAD(P)+ + H2O
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sMMO
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?
chloropentane + NAD(P)H + O2
chloropentanol + NAD(P)+ + H2O
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sMMO
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?
cis-1,3-dimethylcyclohexane + NAD(P)H + O2
3,5-dimethylcyclohexanol + 1-cis-3-dimethylcyclohexanol + NAD(P)+ + H2O + 1-trans-3-dimethylcyclohexanol
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1-trans-3-dimethylcyclohexanol is produced in a low concentration
?
cis-1,4-dimethylcyclohexane + NAD(P)H + O2
1-cis-4-dimethylcyclohexanol + NAD(P)+ + H2O + trans-2,5-dimethylcyclohexanol
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trans-2,5-dimethylcyclohexanol is produced in a low concentration
?
cis-2-butene + NAD(P)H + O2
cis-2,3-epoxybutane + cis-2-buten-1-ol + 2-butanone + NAD(P)+ + H2O
CO + NAD(P)H + O2
CO2 + NAD(P)+ + H2O
cycloheptanecarboxylate + NADH + H+ + O2
trans-4-hydroxycycloheptane-1-carboxylate + NAD+ + H2O
cyclohexane + NAD(P)H + O2
cyclohexanol + NAD(P)+ + H2O
cyclohexanecarboxylate + NADH + H+ + O2
trans-4-hydroxycyclohexane-1-carboxylate + NAD+ + H2O
cyclohexene + NAD(P)H + O2
epoxycyclohexane + 2-cyclohexen-1-ol + NAD(P)+ + H2O
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?
cyclopentanecarboxylate + NADH + H+ + O2
trans-3-hydroxycyclopentane-1-carboxylate + NAD+ + H2O
cytochrome c + NAD(P)H + O2
reduced cytochrome c + NAD(P)+ + H2O
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sMMO
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?
dichloroethane + NADH + O2
ethanol + 2 Cl- + NAD+ + H2O
dichloromethane + NAD(P)H + O2
CO + Cl- + NAD(P)+ + H2O
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-
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?
dichloropropane + NADH + O2
propanol + 2 Cl- + NAD+ + H2O
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?
diethyl ether + NAD(P)H + O2
ethanol + ethanal + NAD(P)+ + H2O
difluoromethane + NADH + O2
difluoromethanol + NAD+ + H2O
dimethyl ether + NAD(P)H + O2
methanol + formaldehyde + NAD(P)+ + H2O
dimethyl ether + NADH + H+ + O2
?
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?
ethane + NAD(P)H + O2
ethanol + NAD(P)+ + H2O
ethane + NADH + O2
?
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?
ethane + NADH + O2
ethanol + NAD+ + H2O
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?
ethene + NAD(P)H + O2
epoxyethane + NAD(P)+ + H2O
ethylbenzene + NAD(P)H + H+ + O2
1-phenylethanol + 3-ethylphenol + 4-ethylphenol + NAD(P)+ + H2O
-
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?
ethylbenzene + NAD(P)H + H+ + O2
?
molecular dynamics simulation to rationalize regioselective hydroxylation of aromatic substrates
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?
fluorobenzene + NAD(P)H + O2
fluorophenol + NAD(P)+ + H2O
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sMMO
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?
fluoromethane + NADH + O2
fluoromethanol + NAD+ + H2O
formate + NAD(P)H + O2
?
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assay with whole cells
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?
furan + NAD(P)H + O2
?
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?
furan + NADH + O2
? + NAD+ + H2O
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?
heptane + NAD(P)H + O2
1-heptanol + 2-heptanol + NAD(P)+ + H2O
heptane + NADH + O2
1-heptanol + 2-heptanol + NAD+ + H2O
-
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-
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?
heptanoate + NADPH + H+ + O2
? + NADP+ + H2O
hexane + NAD(P)H + O2
1-hexanol + 2-hexanol + NAD(P)+ + H2O
hexanoate + NADH + H+ + O2
? + NAD+ + H2O
isobutane + NAD(P)H + O2
2-methyl-1-propanol + 2-methyl-2-propanol + NADP+ + H2O
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-
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?
isopentane + NAD(P)H + O2
2-methylbutan-1-ol + 3-methylbutan-1-ol + 2-methylbutan-2-ol + 3-methylbutan-2-ol + NADP+ + H2O
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?
methane + duroquinol + O2
methanol + duroquinone + H2O
methane + NAD(P)H + H+ + O2
methanol + NAD(P)+ + H2O
methane + NAD(P)H + O2
methanol + NAD(P)+ + H2O
methane + NADH + H+ + O2
methanol + H2O + NAD+
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?
methane + NADH + H+ + O2
methanol + NAD+ + H2O
methane + NADH + O2
methanol + NAD+ + H2O
methane + reduced acceptor + H* + O2
methanol + acceptor + H2O
methane + trans-dichloroethylene + vinyl chloride + trichloroethylene + ?
formaldehyde + ?
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each of these compounds is completely degraded by sMMO-expressing cells when initial concentrations are either 0.01 or 0.03 mM
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?
methanol + NADH + H+ + O2
? + H2O + NAD+
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substrate of intermediate species, Hperoxo and Q, kinetics, overview
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?
methylamine + NADH + H+ + O2
hydroxymethylamine + H2O + NAD+
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substrate of intermediate species, Hperoxo and Q, kinetics, overview
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?
methylcyanide + NADH + H+ + O2
hydroxymethylcyanide + H2O + NAD+
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substrate of intermediate species, Hperoxo and Q, kinetics, and proposed mechanism of CH3CN hydroxylation by Hperoxo, overview
-
-
?
methylene cyclohexane + NAD(P)H + O2
1-cyclohexane-1-methanol + methylene cyclohexane oxide + 4-hydroxymethylene cyclohexane + NAD(P)+ + H2O
-
-
-
?
naphthalene + NAD(P)H + H+ + O2
alpha-naphthol + beta-naphthol + NAD(P)+ + H2O
-
-
-
-
?
naphthalene + NAD(P)H + O2
alpha-naphthol + beta-naphthol + NAD(P)+ + H2O
naphthalene + NADH + H+
alpha-naphthol + beta-naphthol + NAD+ + H2O
nitrobenzene + NADH + O2
nitrophenol + NAD+ + H2O
nitromethane + NADH + H+ + O2
?
-
-
-
-
?
octane + NAD(P)H + O2
1-octanol + 2-octanol + NAD(P)+ + H2O
-
-
-
?
pentane + NAD(P)H + O2
1-pentanol + 2-pentanol + NAD(P)+ + H2O
phenylalanine + NAD(P)H + O2
tyrosine + NAD(P)+ + H2O
-
-
-
?
propane + NAD(P)H + O2
1-propanol + 2-propanol + NAD(P)+ + H2O
propene + NAD(P)H + O2
1,2-epoxypropane + NAD(P)+ + H2O
propene + NADH + H+ + O2
epoxypropane + NAD+ + H2O
propylaldehyde + NADH + H+ + O2
? + H2O + NAD+
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substrate of intermediate species, Hperoxo and Q, kinetics, overview
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-
?
propylene + duroquinol + O2
propylene oxide + reduced duroquinol + H2O
-
-
-
-
?
propylene + NAD(P)H + O2
propylene oxide + NADP+ + H2O
propylene + NADH + H+ + O2
propylene epoxide + NAD+ + H2O
-
-
-
-
?
propylene + NADH + H+ + O2
propylene oxide + NAD+ + H2O
-
-
-
?
propylene + NADH + O2
propylene epoxide + NAD+ + H2O
propylene + NADH + O2
propylene oxide + NAD+ + H2O
pyridine + NAD(P)H + O2
pyridine N-oxide + NAD(P)+ + H2O
-
-
-
?
pyridine + NADH + H+ + O2
?
-
-
-
-
?
styrene + NAD(P)H + O2
styrene epoxide + NAD(P)+ + H2O
styrene + NADH + H+ + O2
?
-
-
-
-
?
toluene + NAD(P)H + H+ + O2
?
molecular dynamics simulation to rationalize regioselective hydroxylation of aromatic substrates
-
-
?
toluene + NAD(P)H + H+ + O2
benzyl alcohol + cresol + NAD(P)+ + H2O
-
-
-
-
?
toluene + NAD(P)H + H+ + O2
benzyl alcohol + NAD(P)+ + H2O
-
-
-
?
toluene + NAD(P)H + H+ + O2
benzyl alcohol + p-cresol + NAD(P)+ + H2O
-
-
-
?
toluene + NAD(P)H + H+ + O2
cresol + NAD(P)+ + H2O
-
sMMO
-
?
toluene + NADH + H+ + O2
?
trans-2-butene + NAD(P)H + O2
trans-2,3-epoxybutane + trans-2-buten-1-ol + NAD(P)+ + H2O
trichloromethane + NAD(P)H + O2
CO2 + Cl- + NAD(P)+ + H2O
-
-
-
?
trichloromethane + NADH + H+ + O2
?
-
-
-
-
?
xylene + NAD(P)H + O2
xylenol + NAD(P)+ + H2O
-
sMMO
-
?
additional information
?
-
1-butene + NAD(P)H + O2

1,2-epoxybutane + NAD(P)+ + H2O
-
-
-
?
1-butene + NAD(P)H + O2
1,2-epoxybutane + NAD(P)+ + H2O
-
-
-
?
benzene + NAD(P)H + H+ + O2

phenol + hydroquinone + NAD(P)+ + H2O
-
-
-
?
benzene + NAD(P)H + H+ + O2
phenol + hydroquinone + NAD(P)+ + H2O
-
-
-
?
benzene + NAD(P)H + H+ + O2

phenol + NAD(P)+ + H2O
-
-
-
?
benzene + NAD(P)H + H+ + O2
phenol + NAD(P)+ + H2O
-
-
-
?
benzene + NADH + H+ + O2

?