1.14.13.25 1,1,2,2-tetramethylcyclopropane + NADH + O2 - Methylosinus trichosporium ? - ? 386930 1.14.13.25 1-butene + NAD(P)H + O2 - Methylococcus capsulatus 1,2-epoxybutane + NAD(P)+ + H2O - ? 288421 1.14.13.25 1-butene + NAD(P)H + O2 - Methylosinus trichosporium 1,2-epoxybutane + NAD(P)+ + H2O - ? 288421 1.14.13.25 2,3-dimethylpentane + NAD(P)H + O2 - Methylococcus capsulatus 3,4-dimethylpentan-2-ol + NAD(P)+ + H2O - ? 288451 1.14.13.25 2-methylpropane + NAD(P)H + O2 - Methylococcus capsulatus 2-methylpropan-2-ol + 2-methylpropan-1-ol + NAD(P)+ + H2O - ? 288450 1.14.13.25 adamantane + NAD(P)H + O2 - Methylococcus capsulatus 1-adamantanol + 2-adamantanol + NAD(P)+ + H2O - ? 288452 1.14.13.25 ammonia + NAD(P)H + O2 - Methylococcus capsulatus hydroxylamine + NAD(P)+ + H2O - ? 288447 1.14.13.25 ammonia + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 416566 1.14.13.25 benzene + NAD(P)H + H+ + O2 - Methylococcus capsulatus phenol + hydroquinone + NAD(P)+ + H2O - ? 288436 1.14.13.25 benzene + NAD(P)H + H+ + O2 - Methylosinus trichosporium phenol + NAD(P)+ + H2O - ? 288437 1.14.13.25 benzene + NAD(P)H + H+ + O2 - Methylocystis sp. phenol + NAD(P)+ + H2O - ? 288437 1.14.13.25 benzene + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 416675 1.14.13.25 benzene + NADH + H+ + O2 - Methylosinus sporium ? - ? 416675 1.14.13.25 benzene + NADH + H+ + O2 - Methylosinus sporium 5 ? - ? 416675 1.14.13.25 benzene + NADH + H+ + O2 - Methylosinus sporium ATCC 35069 ? - ? 416675 1.14.13.25 beta-pinene + NAD(P)H + O2 - Methylococcus capsulatus 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-methanol + beta-pinene oxide + NAD(P)+ + H2O - ? 288454 1.14.13.25 biphenyl + NAD(P)H + H+ + O2 - Methylosinus trichosporium 2-hydroxybiphenyl + 4-hydroxybiphenyl + NAD(P)+ + H2O - ? 396614 1.14.13.25 bromobenzene + NAD(P)H + O2 sMMO Methylocystis sp. bromophenol + NAD(P)+ + H2O - ? 288461 1.14.13.25 bromomethane + NAD(P)H + O2 - Methylococcus capsulatus ? - ? 288448 1.14.13.25 bromomethane + NAD(P)H + O2 - Methylococcus capsulatus Bath ? - ? 288448 1.14.13.25 bromomethane + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 416734 1.14.13.25 butane + NAD(P)H + O2 - Methylococcus capsulatus 1-butanol + 2-butanol + NAD(P)+ + H2O - ? 288427 1.14.13.25 butane + NAD(P)H + O2 - Methylosinus trichosporium 1-butanol + 2-butanol + NAD(P)+ + H2O - ? 288427 1.14.13.25 butane + NAD(P)H + O2 - Methylocystis sp. 1-butanol + 2-butanol + NAD(P)+ + H2O only 2-butanol, sMMO ? 288427 1.14.13.25 butylene + NAD(P)H + O2 sMMO Methylocystis sp. butylene oxide + NAD(P)+ + H2O - ? 288425 1.14.13.25 carbon monoxide + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 416748 1.14.13.25 chlorobenzene + NAD(P)H + O2 sMMO Methylocystis sp. chlorophenol + NAD(P)+ + H2O - ? 288459 1.14.13.25 chloromethane + NAD(P)H + O2 - Methylococcus capsulatus formaldehyde + NAD(P)+ + H2O + ? - ? 288443 1.14.13.25 chloromethane + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 416767 1.14.13.25 chloronaphthalene + NAD(P)H + O2 sMMO Methylocystis sp. chloronaphthol + NAD(P)+ + H2O - ? 288462 1.14.13.25 chloropentane + NAD(P)H + O2 sMMO Methylocystis sp. chloropentanol + NAD(P)+ + H2O - ? 288458 1.14.13.25 cis-1,3-dimethylcyclohexane + NAD(P)H + O2 - Methylococcus capsulatus 3,5-dimethylcyclohexanol + 1-cis-3-dimethylcyclohexanol + NAD(P)+ + H2O + 1-trans-3-dimethylcyclohexanol 1-trans-3-dimethylcyclohexanol is produced in a low concentration ? 288453 1.14.13.25 cis-1,4-dimethylcyclohexane + NAD(P)H + O2 - Methylococcus capsulatus 1-cis-4-dimethylcyclohexanol + NAD(P)+ + H2O + trans-2,5-dimethylcyclohexanol trans-2,5-dimethylcyclohexanol is produced in a low concentration ? 288449 1.14.13.25 cis-2-butene + NAD(P)H + O2 - Methylococcus capsulatus cis-2,3-epoxybutane + cis-2-buten-1-ol + 2-butanone + NAD(P)+ + H2O - ? 288413 1.14.13.25 cis-2-butene + NAD(P)H + O2 - Methylosinus trichosporium cis-2,3-epoxybutane + cis-2-buten-1-ol + 2-butanone + NAD(P)+ + H2O - ? 288413 1.14.13.25 cis-2-butene + NAD(P)H + O2 - Methylococcus capsulatus Bath cis-2,3-epoxybutane + cis-2-buten-1-ol + 2-butanone + NAD(P)+ + H2O - ? 288413 1.14.13.25 CO + NAD(P)H + O2 - Methylococcus capsulatus CO2 + NAD(P)+ + H2O - ? 288412 1.14.13.25 CO + NAD(P)H + O2 - Methylosinus trichosporium CO2 + NAD(P)+ + H2O - ? 288412 1.14.13.25 CO + NAD(P)H + O2 - Methylococcus capsulatus Bath CO2 + NAD(P)+ + H2O - ? 288412 1.14.13.25 cycloheptanecarboxylate + NADH + H+ + O2 - Paraburkholderia terrae trans-4-hydroxycycloheptane-1-carboxylate + NAD+ + H2O - ? 462388 1.14.13.25 cycloheptanecarboxylate + NADH + H+ + O2 - Paraburkholderia terrae KU-64 trans-4-hydroxycycloheptane-1-carboxylate + NAD+ + H2O - ? 462388 1.14.13.25 cyclohexane + NAD(P)H + O2 - Methylococcus capsulatus cyclohexanol + NAD(P)+ + H2O - ? 288434 1.14.13.25 cyclohexane + NAD(P)H + O2 - Methylosinus trichosporium cyclohexanol + NAD(P)+ + H2O - ? 288434 1.14.13.25 cyclohexane + NAD(P)H + O2 sMMO Methylocystis sp. cyclohexanol + NAD(P)+ + H2O - ? 288434 1.14.13.25 cyclohexanecarboxylate + NADH + H+ + O2 - Paraburkholderia terrae trans-4-hydroxycyclohexane-1-carboxylate + NAD+ + H2O - ? 462393 1.14.13.25 cyclohexanecarboxylate + NADH + H+ + O2 - Paraburkholderia terrae KU-64 trans-4-hydroxycyclohexane-1-carboxylate + NAD+ + H2O - ? 462393 1.14.13.25 cyclohexene + NAD(P)H + O2 - Methylosinus trichosporium epoxycyclohexane + 2-cyclohexen-1-ol + NAD(P)+ + H2O - ? 288435 1.14.13.25 cyclopentanecarboxylate + NADH + H+ + O2 - Paraburkholderia terrae trans-3-hydroxycyclopentane-1-carboxylate + NAD+ + H2O - ? 462399 1.14.13.25 cyclopentanecarboxylate + NADH + H+ + O2 - Paraburkholderia terrae KU-64 trans-3-hydroxycyclopentane-1-carboxylate + NAD+ + H2O - ? 462399 1.14.13.25 cytochrome c + NAD(P)H + O2 sMMO Methylocystis sp. reduced cytochrome c + NAD(P)+ + H2O - ? 288457 1.14.13.25 dichloroethane + NADH + O2 - Methylosinus sporium ethanol + 2 Cl- + NAD+ + H2O - ? 462434 1.14.13.25 dichloroethane + NADH + O2 - Methylosinus sporium 5 ethanol + 2 Cl- + NAD+ + H2O - ? 462434 1.14.13.25 dichloroethane + NADH + O2 - Methylosinus sporium ATCC 35069 ethanol + 2 Cl- + NAD+ + H2O - ? 462434 1.14.13.25 dichloromethane + NAD(P)H + O2 - Methylococcus capsulatus CO + Cl- + NAD(P)+ + H2O - ? 288444 1.14.13.25 dichloropropane + NADH + O2 - Methylosinus sporium propanol + 2 Cl- + NAD+ + H2O - ? 462435 1.14.13.25 diethyl ether + NAD(P)H + O2 - Methylococcus capsulatus ethanol + ethanal + NAD(P)+ + H2O - ? 288414 1.14.13.25 diethyl ether + NAD(P)H + O2 sMMO Methylocystis sp. ethanol + ethanal + NAD(P)+ + H2O - ? 288414 1.14.13.25 diethyl ether + NAD(P)H + O2 - Methylococcus capsulatus Bath ethanol + ethanal + NAD(P)+ + H2O - ? 288414 1.14.13.25 diethyl ether + NAD(P)H + O2 sMMO Methylocystis sp. WI 14 ethanol + ethanal + NAD(P)+ + H2O - ? 288414 1.14.13.25 difluoromethane + NADH + O2 soluble enzyme Methylococcus capsulatus difluoromethanol + NAD+ + H2O - ? 388533 1.14.13.25 difluoromethane + NADH + O2 soluble enzyme Methylococcus capsulatus Bath difluoromethanol + NAD+ + H2O - ? 388533 1.14.13.25 dimethyl ether + NAD(P)H + O2 - Methylococcus capsulatus methanol + formaldehyde + NAD(P)+ + H2O - ? 288415 1.14.13.25 dimethyl ether + NAD(P)H + O2 no activity Methylosinus trichosporium methanol + formaldehyde + NAD(P)+ + H2O - ? 288415 1.14.13.25 dimethyl ether + NAD(P)H + O2 - Methylococcus capsulatus Bath methanol + formaldehyde + NAD(P)+ + H2O - ? 288415 1.14.13.25 dimethyl ether + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 416923 1.14.13.25 ethane + NAD(P)H + O2 - Methylococcus capsulatus ethanol + NAD(P)+ + H2O - ? 288422 1.14.13.25 ethane + NAD(P)H + O2 - Methylosinus trichosporium ethanol + NAD(P)+ + H2O - ? 288422 1.14.13.25 ethane + NADH + O2 - Methylosinus trichosporium ethanol + NAD+ + H2O - ? 376766 1.14.13.25 ethane + NADH + O2 - Methylosinus trichosporium ? - ? 388659 1.14.13.25 ethene + NAD(P)H + O2 - Methylococcus capsulatus epoxyethane + NAD(P)+ + H2O - ? 288419 1.14.13.25 ethene + NAD(P)H + O2 sMMO Methylocystis sp. epoxyethane + NAD(P)+ + H2O - ? 288419 1.14.13.25 ethene + NAD(P)H + O2 - Methylococcus capsulatus Bath epoxyethane + NAD(P)+ + H2O - ? 288419 1.14.13.25 ethene + NAD(P)H + O2 sMMO Methylocystis sp. WI 14 epoxyethane + NAD(P)+ + H2O - ? 288419 1.14.13.25 ethylbenzene + NAD(P)H + H+ + O2 - Methylosinus trichosporium 1-phenylethanol + 3-ethylphenol + 4-ethylphenol + NAD(P)+ + H2O - ? 397147 1.14.13.25 ethylbenzene + NAD(P)H + H+ + O2 molecular dynamics simulation to rationalize regioselective hydroxylation of aromatic substrates Methylosinus trichosporium OB3b ? - ? 443547 1.14.13.25 fluorobenzene + NAD(P)H + O2 sMMO Methylocystis sp. fluorophenol + NAD(P)+ + H2O - ? 288460 1.14.13.25 fluoromethane + NADH + O2 soluble enzyme Methylococcus capsulatus fluoromethanol + NAD+ + H2O - ? 388696 1.14.13.25 fluoromethane + NADH + O2 soluble enzyme Methylococcus capsulatus Bath fluoromethanol + NAD+ + H2O - ? 388696 1.14.13.25 formate + NAD(P)H + O2 assay with whole cells Methylosinus trichosporium ? - ? 288456 1.14.13.25 furan + NAD(P)H + O2 - Methylosinus trichosporium ? - ? 288463 1.14.13.25 furan + NADH + O2 - Methylosinus trichosporium ? + NAD+ + H2O - ? 376813 1.14.13.25 heptane + NAD(P)H + O2 - Methylococcus capsulatus 1-heptanol + 2-heptanol + NAD(P)+ + H2O - ? 288432 1.14.13.25 heptane + NAD(P)H + O2 sMMO Methylocystis sp. 1-heptanol + 2-heptanol + NAD(P)+ + H2O position of hydroxylation cannot be determined exactly ? 288432 1.14.13.25 heptane + NADH + O2 - Methylosinus sporium 1-heptanol + 2-heptanol + NAD+ + H2O - ? 462566 1.14.13.25 heptanoate + NADPH + H+ + O2 - Paraburkholderia terrae ? + NADP+ + H2O - ? 462567 1.14.13.25 heptanoate + NADPH + H+ + O2 - Paraburkholderia terrae KU-64 ? + NADP+ + H2O - ? 462567 1.14.13.25 hexane + NAD(P)H + O2 - Methylococcus capsulatus 1-hexanol + 2-hexanol + NAD(P)+ + H2O - ? 288431 1.14.13.25 hexane + NAD(P)H + O2 sMMO Methylocystis sp. 1-hexanol + 2-hexanol + NAD(P)+ + H2O position of hydroxylation cannot be determined exactly ? 288431 1.14.13.25 hexanoate + NADH + H+ + O2 - Paraburkholderia terrae ? + NAD+ + H2O - ? 462572 1.14.13.25 hexanoate + NADH + H+ + O2 - Paraburkholderia terrae KU-64 ? + NAD+ + H2O - ? 462572 1.14.13.25 isobutane + NAD(P)H + O2 - Methylosinus trichosporium 2-methyl-1-propanol + 2-methyl-2-propanol + NADP+ + H2O - ? 288428 1.14.13.25 isopentane + NAD(P)H + O2 - Methylosinus trichosporium 2-methylbutan-1-ol + 3-methylbutan-1-ol + 2-methylbutan-2-ol + 3-methylbutan-2-ol + NADP+ + H2O - ? 288429 1.14.13.25 methane + duroquinol + O2 - Methylococcus capsulatus methanol + duroquinone + H2O - ? 389158 1.14.13.25 methane + duroquinol + O2 - Methylomicrobium album methanol + duroquinone + H2O - ? 389158 1.14.13.25 methane + duroquinol + O2 - Methylocystis sp. methanol + duroquinone + H2O - ? 389158 1.14.13.25 methane + duroquinol + O2 - Methylococcus capsulatus Bath methanol + duroquinone + H2O - ? 389158 1.14.13.25 methane + duroquinol + O2 - Methylomicrobium album BG8 methanol + duroquinone + H2O - ? 389158 1.14.13.25 methane + NAD(P)H + H+ + O2 - Methylosinus trichosporium methanol + NAD(P)+ + H2O - ? 397745 1.14.13.25 methane + NAD(P)H + H+ + O2 - Methylococcus capsulatus methanol + NAD(P)+ + H2O - ? 397745 1.14.13.25 methane + NAD(P)H + H+ + O2 methane hydroxylation through methane monooxygenases is a key aspect due to their control of the carbon cycle in the ecology system Methylococcus capsulatus methanol + NAD(P)+ + H2O - ? 397745 1.14.13.25 methane + NAD(P)H + H+ + O2 methane hydroxylation through methane monooxygenases is a key aspect due to their control of the carbon cycle in the ecology system Methylosinus trichosporium methanol + NAD(P)+ + H2O - ? 397745 1.14.13.25 methane + NAD(P)H + H+ + O2 presentation of experimental and computational data consistent with an open-core structure for the key intermediate in methane oxidation Methylosinus trichosporium methanol + NAD(P)+ + H2O - ? 397745 1.14.13.25 methane + NAD(P)H + H+ + O2 - Methylococcus capsulatus Bath. methanol + NAD(P)+ + H2O - ? 397745 1.14.13.25 methane + NAD(P)H + H+ + O2 methane hydroxylation through methane monooxygenases is a key aspect due to their control of the carbon cycle in the ecology system Methylococcus capsulatus Bath. methanol + NAD(P)+ + H2O - ? 397745 1.14.13.25 methane + NAD(P)H + O2 - Methylococcus capsulatus methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 - Methylosinus trichosporium methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 - Methylobacterium sp. methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 - Methylosinus sporium methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 - Methylosinus trichosporium OB3b methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 - Methylocystis sp. methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 initial step in the assimilation of methane in bacteria that grow with methane as sole carbon and energy source Methylococcus capsulatus methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 consists of three subunits, the hydroxylase (MMOH), at which the oxidation of methane takes place, the reductase (MMOR) and a small regulating unit MMOB Bacteria methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 - Methylosinus sporium 5 methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 - Methylococcus capsulatus Bath methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 initial step in the assimilation of methane in bacteria that grow with methane as sole carbon and energy source Methylococcus capsulatus Bath methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 - Methylocystis sp. WI 14 methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NAD(P)H + O2 - Methylosinus trichosporium IMV 3011 methanol + NAD(P)+ + H2O - ? 288411 1.14.13.25 methane + NADH + H+ + O2 - Methylococcus capsulatus methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylosinus trichosporium methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylomonas sp. methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylomonas methanica methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylosinus sporium methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylocystis sp. methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylosinus sporium 5 methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylococcus capsulatus Bath methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylomonas methanica MC09 methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylococcus capsulatus Bath. methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylococcus capsulatus HD6T methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylosinus sporium ATCC 35069 methanol + NAD+ + H2O - ? 397746 1.14.13.25 methane + NADH + H+ + O2 - Methylococcus capsulatus methanol + H2O + NAD+ - ? 413459 1.14.13.25 methane + NADH + O2 - Methylococcus capsulatus methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 - Methylosinus trichosporium methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 - methylotrophic bacterium methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 - Crenothrix polyspora methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 methane is oxidized to methanol with 100% efficiency with no over-oxidation, methanol is then further oxidized by other enzymes in two electron steps to CO2 Methylophilaceae methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 via diiron(IV) reaction intermediate Q, the decay rate of intermediate Q is substantially accelerated in the presence of fluuoromethane and difluoromethane Methylococcus capsulatus methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 for the MMOH alone the rate of turnover is increased 150fold and rate constant for O2 binding is increased 1000fold in the binary complex compared to the complete enzyme Methylophilaceae methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 modeling intermolecular electron transfer in the sMMO system, interconversion of rapid and slow electron-transfer pathways, overview Methylococcus capsulatus methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 - Methylococcus capsulatus Bath methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 via diiron(IV) reaction intermediate Q, the decay rate of intermediate Q is substantially accelerated in the presence of fluuoromethane and difluoromethane Methylococcus capsulatus Bath methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + NADH + O2 modeling intermolecular electron transfer in the sMMO system, interconversion of rapid and slow electron-transfer pathways, overview Methylococcus capsulatus Bath methanol + NAD+ + H2O - ? 377156 1.14.13.25 methane + reduced acceptor + H* + O2 - Methylococcus capsulatus methanol + acceptor + H2O - ? 448353 1.14.13.25 methane + reduced acceptor + H* + O2 - Methylomicrobium album methanol + acceptor + H2O - ? 448353 1.14.13.25 methane + reduced acceptor + H* + O2 - Methylocystis sp. methanol + acceptor + H2O - ? 448353 1.14.13.25 methane + reduced acceptor + H* + O2 - Methylococcus capsulatus Bath methanol + acceptor + H2O - ? 448353 1.14.13.25 methane + reduced acceptor + H* + O2 - Methylomicrobium album BG8 methanol + acceptor + H2O - ? 448353 1.14.13.25 methane + trans-dichloroethylene + vinyl chloride + trichloroethylene + ? each of these compounds is completely degraded by sMMO-expressing cells when initial concentrations are either 0.01 or 0.03 mM Methylosinus trichosporium formaldehyde + ? - ? 417256 1.14.13.25 methanol + NADH + H+ + O2 substrate of intermediate species, Hperoxo and Q, kinetics, overview Methylococcus capsulatus ? + H2O + NAD+ - ? 414848 1.14.13.25 methylamine + NADH + H+ + O2 substrate of intermediate species, Hperoxo and Q, kinetics, overview Methylococcus capsulatus hydroxymethylamine + H2O + NAD+ - ? 414867 1.14.13.25 methylcyanide + NADH + H+ + O2 substrate of intermediate species, Hperoxo and Q, kinetics, and proposed mechanism of CH3CN hydroxylation by Hperoxo, overview Methylococcus capsulatus hydroxymethylcyanide + H2O + NAD+ - ? 414868 1.14.13.25 methylene cyclohexane + NAD(P)H + O2 - Methylococcus capsulatus 1-cyclohexane-1-methanol + methylene cyclohexane oxide + 4-hydroxymethylene cyclohexane + NAD(P)+ + H2O - ? 288455 1.14.13.25 additional information broad specificity Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information very non-specific oxygenase Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information oxidation of norborneols Methylosinus trichosporium ? - ? 89 1.14.13.25 additional information oxidation of deuterated compounds Methylosinus trichosporium ? - ? 89 1.14.13.25 additional information sMMO expressed at low copper concentration shows low substrate specificity, while pMMO expressed at high copper concentration shows high substrate specificity Methylocystis sp. ? - ? 89 1.14.13.25 additional information cofactor-independent oxygenation reactions catalyzed by soluble methane monooxygenase at the surface of a modified gold electrode Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information access and regulation in the methane monooxygenase system via interaction of reductase protein MMOB and hydroxylase protein MMOH, regulatory effects of MMOB, overview Methylophilaceae ? - ? 89 1.14.13.25 additional information the enzyme expresses the soluble enzyme form under copper limitation, and the membrane-bound particulate MMO at high copper-to-biomass ratio, mechanism of the copper switch involves a tetrameric 480 kDA sensor protein MmoS, encoded by gene mmoS, as part of a two-component signaling system, domain organization, MmoS contains a FAD cofactor, indirect regulation without binding of copper to MmoS, overview Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information a number of substituted methanes, e.g. CH3X (X) H, CH3, OH, CN, NO2, or F, react with MMOH, quantitative modeling of substrate hydroxylation via mixed quantum mechanics/molecular mechanics techniques, overview Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information effects of spin-traps on MMO activity, overview Methylosinus trichosporium ? - ? 89 1.14.13.25 additional information fluoroform is no substrate Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information inactive toward anthracene and phenanthrene Methylosinus trichosporium ? - ? 89 1.14.13.25 additional information the enzyme catalyzes the selective oxidation of methane to methanol, but the enzyme is also capable of hydroxylating and epoxidizing a broad range of hydrocarbon substrates in addition to methane Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information the enzyme catalyzes the selective oxidation of methane to methanol, but is also capable of hydroxylating and epoxidizing a broad range of hydrocarbon substrates in addition to methane. Reactions of the two intermediate species, of Hperoxo and Q, two oxidants that are generated sequentially during the reaction of reduced protein with O, with a panel of substrates of varying C-H bond strength, double-mixing stoppedflow spectroscopy, overview. Three classes of substrates exist according to the rate-determining step in the reaction Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information the sMMO enzyme has broad substrate specificity compared to pMMO Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information the sMMO enzyme has broad substrate specificity compared to pMMO Methylomicrobium album ? - ? 89 1.14.13.25 additional information the sMMO enzyme has broad substrate specificity compared to pMMO Methylocystis sp. ? - ? 89 1.14.13.25 additional information pMMO has broader substrate specificity but lower activity with smaller hydrocarbons like methane, ethane, and propene compared to pMMO Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information pMMO has broader substrate specificity but lower activity with smaller hydrocarbons like methane, ethane, and propene compared to pMMO Methylosinus trichosporium ? - ? 89 1.14.13.25 additional information pMMO has broader substrate specificity but lower activity with smaller hydrocarbons like methane, ethane, and propene compared to pMMO Methylomonas sp. ? - ? 89 1.14.13.25 additional information Methyloferula stellata AR4 is an aerobic acidophilic methanotroph, which, in contrast to most known methanotrophs but similar to Methylocella spp., possesses only a soluble methane monooxygenase Methyloferula stellata AR4 ? - ? 89 1.14.13.25 additional information multicomponent monooxygenase. The ferredoxin domain of the reductase binds to the canyon region of the hydroxylase, previously determined to be the regulatory protein binding site as well. The latter thus inhibits reductase binding to the hydroxylase and, consequently, intermolecular electron transfer from the reductase to the hydroxylase diiron active site. The binding competition between the regulatory protein and the reductase may serve as a control mechanism for regulating electron transfer, and other BMM enzymes are likely to adopt the same mechanism Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information naphthalene assay for sMMO activity Methylosinus trichosporium ? - ? 89 1.14.13.25 additional information the regulatory component (MMOB) of soluble methane monooxygenase (sMMO) has a unique N-terminal tail not found in regulatory proteins of other bacterial multicomponent monooxygenases. This N-terminal tail is indispensable for proper function, yet its solution structure and role in catalysis remain elusive. The oxidation state of the hydroxylase component, MMOH, modulates the conformation of the N-terminal tail in the MMOH-2MMOB complex, which in turn facilitates catalysis. The N-terminal tail switches from a relaxed, flexible conformational state to an ordered state upon MMOH reduction from the diiron(III) to the diiron(II) state Methylococcus capsulatus ? - ? 89 1.14.13.25 additional information a colorimetric assay is adopted for the sMMO activity detection of biofilm Methylosinus trichosporium ? - - 89 1.14.13.25 additional information enzyme sMMO shows oxidation ability of various substrates, including alkanes, alkenes, aromatics, heterocyclics, and chlorinated compounds Methylosinus sporium ? - - 89 1.14.13.25 additional information sMMO is known to oxidize a variety of hydrocarbons, including alkanes ranging from methane to octane. The presence of 1,6-hexanediol near the di-iron center can be explained by the opening of the cavity, mediated by the side-chain rearrangement of Leu110 and Phe188, both of which function together as a gate for substrate and product passage to the active site. While MMOB is known to connect cavities for substrate access, the MMOD-mediated cavity opening appears to be a consequence of MMOHbeta-NT dissociation and subsequent structural relaxation of MMOHalpha. Both substrate ingress and product egress may take place through the substrate access cavity and not through the pore located near the active site, at least for hydrocarbon chain substrates such as hexane Methylosinus sporium ? - - 89 1.14.13.25 additional information the soluble methane monooxygenase receives electrons from NADH via its reductase MmoC for oxidation of methane. The NADH-dependent reductase MmoC produces only trace amounts of superoxide, but mainly hydrogen peroxide during uncoupled turnover reactions Methylomonas methanica ? - - 89 1.14.13.25 additional information enzyme sMMO shows oxidation ability of various substrates, including alkanes, alkenes, aromatics, heterocyclics, and chlorinated compounds Methylosinus sporium 5 ? - - 89 1.14.13.25 additional information sMMO is known to oxidize a variety of hydrocarbons, including alkanes ranging from methane to octane. The presence of 1,6-hexanediol near the di-iron center can be explained by the opening of the cavity, mediated by the side-chain rearrangement of Leu110 and Phe188, both of which function together as a gate for substrate and product passage to the active site. While MMOB is known to connect cavities for substrate access, the MMOD-mediated cavity opening appears to be a consequence of MMOHbeta-NT dissociation and subsequent structural relaxation of MMOHalpha. Both substrate ingress and product egress may take place through the substrate access cavity and not through the pore located near the active site, at least for hydrocarbon chain substrates such as hexane Methylosinus sporium 5 ? - - 89 1.14.13.25 additional information the sMMO enzyme has broad substrate specificity compared to pMMO Methylococcus capsulatus Bath ? - ? 89 1.14.13.25 additional information fluoroform is no substrate Methylococcus capsulatus Bath ? - ? 89 1.14.13.25 additional information the enzyme expresses the soluble enzyme form under copper limitation, and the membrane-bound particulate MMO at high copper-to-biomass ratio, mechanism of the copper switch involves a tetrameric 480 kDA sensor protein MmoS, encoded by gene mmoS, as part of a two-component signaling system, domain organization, MmoS contains a FAD cofactor, indirect regulation without binding of copper to MmoS, overview Methylococcus capsulatus Bath ? - ? 89 1.14.13.25 additional information a number of substituted methanes, e.g. CH3X (X) H, CH3, OH, CN, NO2, or F, react with MMOH, quantitative modeling of substrate hydroxylation via mixed quantum mechanics/molecular mechanics techniques, overview Methylococcus capsulatus Bath ? - ? 89 1.14.13.25 additional information very non-specific oxygenase Methylococcus capsulatus Bath ? - ? 89 1.14.13.25 additional information broad specificity Methylococcus capsulatus Bath ? - ? 89 1.14.13.25 additional information the soluble methane monooxygenase receives electrons from NADH via its reductase MmoC for oxidation of methane. The NADH-dependent reductase MmoC produces only trace amounts of superoxide, but mainly hydrogen peroxide during uncoupled turnover reactions Methylomonas methanica MC09 ? - - 89 1.14.13.25 additional information the regulatory component (MMOB) of soluble methane monooxygenase (sMMO) has a unique N-terminal tail not found in regulatory proteins of other bacterial multicomponent monooxygenases. This N-terminal tail is indispensable for proper function, yet its solution structure and role in catalysis remain elusive. The oxidation state of the hydroxylase component, MMOH, modulates the conformation of the N-terminal tail in the MMOH-2MMOB complex, which in turn facilitates catalysis. The N-terminal tail switches from a relaxed, flexible conformational state to an ordered state upon MMOH reduction from the diiron(III) to the diiron(II) state Methylococcus capsulatus Bath. ? - ? 89 1.14.13.25 additional information multicomponent monooxygenase. The ferredoxin domain of the reductase binds to the canyon region of the hydroxylase, previously determined to be the regulatory protein binding site as well. The latter thus inhibits reductase binding to the hydroxylase and, consequently, intermolecular electron transfer from the reductase to the hydroxylase diiron active site. The binding competition between the regulatory protein and the reductase may serve as a control mechanism for regulating electron transfer, and other BMM enzymes are likely to adopt the same mechanism Methylococcus capsulatus Bath. ? - ? 89 1.14.13.25 additional information pMMO has broader substrate specificity but lower activity with smaller hydrocarbons like methane, ethane, and propene compared to pMMO Methylococcus capsulatus HD6T ? - ? 89 1.14.13.25 additional information the sMMO enzyme has broad substrate specificity compared to pMMO Methylomicrobium album BG8 ? - ? 89 1.14.13.25 additional information sMMO expressed at low copper concentration shows low substrate specificity, while pMMO expressed at high copper concentration shows high substrate specificity Methylocystis sp. WI 14 ? - ? 89 1.14.13.25 additional information enzyme sMMO shows oxidation ability of various substrates, including alkanes, alkenes, aromatics, heterocyclics, and chlorinated compounds Methylosinus sporium ATCC 35069 ? - - 89 1.14.13.25 additional information sMMO is known to oxidize a variety of hydrocarbons, including alkanes ranging from methane to octane. The presence of 1,6-hexanediol near the di-iron center can be explained by the opening of the cavity, mediated by the side-chain rearrangement of Leu110 and Phe188, both of which function together as a gate for substrate and product passage to the active site. While MMOB is known to connect cavities for substrate access, the MMOD-mediated cavity opening appears to be a consequence of MMOHbeta-NT dissociation and subsequent structural relaxation of MMOHalpha. Both substrate ingress and product egress may take place through the substrate access cavity and not through the pore located near the active site, at least for hydrocarbon chain substrates such as hexane Methylosinus sporium ATCC 35069 ? - - 89 1.14.13.25 naphthalene + NAD(P)H + H+ + O2 - Methylosinus trichosporium alpha-naphthol + beta-naphthol + NAD(P)+ + H2O - ? 397969 1.14.13.25 naphthalene + NAD(P)H + O2 - Methylococcus capsulatus alpha-naphthol + beta-naphthol + NAD(P)+ + H2O - ? 288446 1.14.13.25 naphthalene + NAD(P)H + O2 - Methylosinus trichosporium OB3b alpha-naphthol + beta-naphthol + NAD(P)+ + H2O - ? 288446 1.14.13.25 naphthalene + NAD(P)H + O2 sMMO Methylocystis sp. alpha-naphthol + beta-naphthol + NAD(P)+ + H2O - ? 288446 1.14.13.25 naphthalene + NAD(P)H + O2 oxidized by sMMO Methylococcus capsulatus alpha-naphthol + beta-naphthol + NAD(P)+ + H2O - ? 288446 1.14.13.25 naphthalene + NAD(P)H + O2 oxidized by sMMO Methylosinus trichosporium alpha-naphthol + beta-naphthol + NAD(P)+ + H2O - ? 288446 1.14.13.25 naphthalene + NAD(P)H + O2 oxidized by sMMO Methylomonas sp. GYJ3 alpha-naphthol + beta-naphthol + NAD(P)+ + H2O - ? 288446 1.14.13.25 naphthalene + NAD(P)H + O2 oxidized by sMMO Methylococcus capsulatus HD6T alpha-naphthol + beta-naphthol + NAD(P)+ + H2O - ? 288446 1.14.13.25 naphthalene + NADH + H+ - Methylococcus capsulatus alpha-naphthol + beta-naphthol + NAD+ + H2O - ? 417399 1.14.13.25 naphthalene + NADH + H+ - Methylosinus trichosporium alpha-naphthol + beta-naphthol + NAD+ + H2O - ? 417399 1.14.13.25 naphthalene + NADH + H+ - Methylomonas sp. alpha-naphthol + beta-naphthol + NAD+ + H2O - ? 417399 1.14.13.25 naphthalene + NADH + H+ - Methylococcus capsulatus HD6T alpha-naphthol + beta-naphthol + NAD+ + H2O - ? 417399 1.14.13.25 nitrobenzene + NADH + O2 - Methylosinus trichosporium nitrophenol + NAD+ + H2O - ? 377377 1.14.13.25 nitrobenzene + NADH + O2 an electron is removed from nitrobenzene by Q in the first step of the reaction and then the bound hydroxyl radical formed in this process rebounds to form nitrophenol Methylosinus trichosporium nitrophenol + NAD+ + H2O - ? 377377 1.14.13.25 nitromethane + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 417415 1.14.13.25 octane + NAD(P)H + O2 - Methylococcus capsulatus 1-octanol + 2-octanol + NAD(P)+ + H2O - ? 288433 1.14.13.25 pentane + NAD(P)H + O2 - Methylococcus capsulatus 1-pentanol + 2-pentanol + NAD(P)+ + H2O - ? 288430 1.14.13.25 pentane + NAD(P)H + O2 sMMO Methylocystis sp. 1-pentanol + 2-pentanol + NAD(P)+ + H2O position of hydroxylation cannot be determined exactly ? 288430 1.14.13.25 phenylalanine + NAD(P)H + O2 - Methylococcus capsulatus tyrosine + NAD(P)+ + H2O - ? 288442 1.14.13.25 propane + NAD(P)H + O2 - Methylococcus capsulatus 1-propanol + 2-propanol + NAD(P)+ + H2O - ? 288423 1.14.13.25 propane + NAD(P)H + O2 - Methylosinus trichosporium 1-propanol + 2-propanol + NAD(P)+ + H2O - ? 288423 1.14.13.25 propane + NAD(P)H + O2 - Methylocystis sp. 1-propanol + 2-propanol + NAD(P)+ + H2O only 2-propanol, sMMO ? 288423 1.14.13.25 propane + NAD(P)H + O2 - Methylocystis sp. WI 14 1-propanol + 2-propanol + NAD(P)+ + H2O only 2-propanol, sMMO ? 288423 1.14.13.25 propene + NAD(P)H + O2 - Methylococcus capsulatus 1,2-epoxypropane + NAD(P)+ + H2O - ? 288420 1.14.13.25 propene + NAD(P)H + O2 - Methylosinus trichosporium 1,2-epoxypropane + NAD(P)+ + H2O - ? 288420 1.14.13.25 propene + NAD(P)H + O2 - Methylomonas sp. GYJ3 1,2-epoxypropane + NAD(P)+ + H2O - ? 288420 1.14.13.25 propene + NAD(P)H + O2 - Methylococcus capsulatus Bath 1,2-epoxypropane + NAD(P)+ + H2O - ? 288420 1.14.13.25 propene + NAD(P)H + O2 - Methylococcus capsulatus HD6T 1,2-epoxypropane + NAD(P)+ + H2O - ? 288420 1.14.13.25 propene + NADH + H+ + O2 - Methylococcus capsulatus epoxypropane + NAD+ + H2O - ? 417527 1.14.13.25 propene + NADH + H+ + O2 - Methylosinus trichosporium epoxypropane + NAD+ + H2O - ? 417527 1.14.13.25 propene + NADH + H+ + O2 - Methylomonas sp. epoxypropane + NAD+ + H2O - ? 417527 1.14.13.25 propylaldehyde + NADH + H+ + O2 substrate of intermediate species, Hperoxo and Q, kinetics, overview Methylococcus capsulatus ? + H2O + NAD+ - ? 415160 1.14.13.25 propylene + duroquinol + O2 - Methylosinus trichosporium propylene oxide + reduced duroquinol + H2O - ? 377552 1.14.13.25 propylene + NAD(P)H + O2 enzyme form sMMO Methylococcus capsulatus propylene oxide + NADP+ + H2O - ? 288424 1.14.13.25 propylene + NAD(P)H + O2 enzyme form sMMO Methylocystis sp. propylene oxide + NADP+ + H2O - ? 288424 1.14.13.25 propylene + NAD(P)H + O2 enzyme form sMMO Methylococcus capsulatus Bath propylene oxide + NADP+ + H2O - ? 288424 1.14.13.25 propylene + NADH + H+ + O2 - Methylosinus trichosporium propylene epoxide + NAD+ + H2O - ? 398193 1.14.13.25 propylene + NADH + H+ + O2 - Methylococcus capsulatus propylene oxide + NAD+ + H2O - ? 417543 1.14.13.25 propylene + NADH + O2 - Methylococcus capsulatus propylene oxide + NAD+ + H2O - ? 377553 1.14.13.25 propylene + NADH + O2 the peroxodiiron(III) intermediate that precedes Q formation in the catalytic cycle has been demonstrated to react with propylene Methylococcus capsulatus propylene oxide + NAD+ + H2O - ? 377553 1.14.13.25 propylene + NADH + O2 the peroxodiiron(III) intermediate that precedes Q formation in the catalytic cycle has been demonstrated to react with propylene Methylococcus capsulatus Bath propylene oxide + NAD+ + H2O - ? 377553 1.14.13.25 propylene + NADH + O2 - Methylococcus capsulatus Bath propylene oxide + NAD+ + H2O - ? 377553 1.14.13.25 propylene + NADH + O2 - Methylococcus capsulatus propylene epoxide + NAD+ + H2O - ? 389607 1.14.13.25 propylene + NADH + O2 - Methylosinus trichosporium propylene epoxide + NAD+ + H2O - ? 389607 1.14.13.25 propylene + NADH + O2 - Methylococcus capsulatus Bath propylene epoxide + NAD+ + H2O - ? 389607 1.14.13.25 propylene + NADH + O2 - Methylosinus trichosporium IMV 3011 propylene epoxide + NAD+ + H2O - ? 389607 1.14.13.25 pyridine + NAD(P)H + O2 - Methylococcus capsulatus pyridine N-oxide + NAD(P)+ + H2O - ? 288417 1.14.13.25 pyridine + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 417553 1.14.13.25 styrene + NAD(P)H + O2 - Methylococcus capsulatus styrene epoxide + NAD(P)+ + H2O - ? 288416 1.14.13.25 styrene + NAD(P)H + O2 - Methylococcus capsulatus Bath styrene epoxide + NAD(P)+ + H2O - ? 288416 1.14.13.25 styrene + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 417647 1.14.13.25 toluene + NAD(P)H + H+ + O2 sMMO Methylocystis sp. cresol + NAD(P)+ + H2O - ? 288438 1.14.13.25 toluene + NAD(P)H + H+ + O2 - Methylococcus capsulatus benzyl alcohol + p-cresol + NAD(P)+ + H2O - ? 288439 1.14.13.25 toluene + NAD(P)H + H+ + O2 - Methylosinus trichosporium benzyl alcohol + NAD(P)+ + H2O - ? 288440 1.14.13.25 toluene + NAD(P)H + H+ + O2 - Methylosinus trichosporium benzyl alcohol + cresol + NAD(P)+ + H2O - ? 398431 1.14.13.25 toluene + NAD(P)H + H+ + O2 molecular dynamics simulation to rationalize regioselective hydroxylation of aromatic substrates Methylosinus trichosporium OB3b ? - ? 443937 1.14.13.25 toluene + NADH + H+ + O2 - Methylosinus sporium ? - ? 389900 1.14.13.25 toluene + NADH + H+ + O2 - Methylosinus sporium 5 ? - ? 389900 1.14.13.25 toluene + NADH + H+ + O2 - Methylosinus sporium ATCC 35069 ? - ? 389900 1.14.13.25 trans-2-butene + NAD(P)H + O2 - Methylococcus capsulatus trans-2,3-epoxybutane + trans-2-buten-1-ol + NAD(P)+ + H2O - ? 288418 1.14.13.25 trans-2-butene + NAD(P)H + O2 - Methylosinus trichosporium trans-2,3-epoxybutane + trans-2-buten-1-ol + NAD(P)+ + H2O - ? 288418 1.14.13.25 trans-2-butene + NAD(P)H + O2 - Methylococcus capsulatus Bath trans-2,3-epoxybutane + trans-2-buten-1-ol + NAD(P)+ + H2O - ? 288418 1.14.13.25 trichloromethane + NAD(P)H + O2 - Methylococcus capsulatus CO2 + Cl- + NAD(P)+ + H2O - ? 288445 1.14.13.25 trichloromethane + NADH + H+ + O2 - Methylococcus capsulatus ? - ? 417716 1.14.13.25 xylene + NAD(P)H + O2 sMMO Methylocystis sp. xylenol + NAD(P)+ + H2O - ? 288441