1.7.3.1: nitroalkane oxidase
This is an abbreviated version!
For detailed information about nitroalkane oxidase, go to the full flat file.
Word Map on EC 1.7.3.1
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1.7.3.1
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atlantic
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oscillation
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climate
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winter
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atmospheric
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orange
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robot
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weather
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acridine
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ocean
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interannual
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summer
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arctic
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nai
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phenology
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cardiolipin
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humanoid
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forecast
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warmer
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nonyl
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rainfall
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meteorological
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hydrological
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seabird
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snow
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latitudinal
- 1.7.3.1
-
atlantic
-
oscillation
-
climate
-
winter
-
atmospheric
- orange
-
robot
-
weather
- acridine
-
ocean
-
interannual
-
summer
-
arctic
- nai
-
phenology
- cardiolipin
-
humanoid
-
forecast
-
warmer
-
nonyl
-
rainfall
-
meteorological
-
hydrological
-
seabird
-
snow
-
latitudinal
Reaction
Synonyms
2-npdl, More, NAO, NaoA, nitroalkane oxidase, nitroalkane-oxidizing enzyme, nitroethane oxidase, nitroethane:oxygen oxidoreductase, NOE, oxidase, nitroethane, PA4202
ECTree
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Substrates Products
Substrates Products on EC 1.7.3.1 - nitroalkane oxidase
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REACTION DIAGRAM
3-nitropropanoic acid + H2O + O2
2-oxopropanoic acid + nitrite + H2O2
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nitroalkane + O2 + H2O
aldehyde or ketone + nitrite + H2O2
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neutral nitroalkanes
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butyraldehyde + nitrite + H2O2
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1-nitrobutane + O2 + H2O
butyraldehyde + nitrite + H2O2
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400fold more effective than nitroethane
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1-nitropropane + H2O + O2
propionaldehyde + nitrite + H2O2
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1-nitropropane + H2O + O2
propionaldehyde + nitrite + H2O2
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2-nitropropane + H2O + O2
acetone + nitrite + H2O2
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ethanal + nitrite + H2O2
solvent isotope and viscositiy effects: the kcat proton inventory is consistent with a single exchangeable proton in flight, while the kcat/KM is consistent with either a single proton in flight in the transition state or a medium effect. Increasing the solvent viscosity does not affect the kcat or kcat/KM value significantly, establishing that nitroethane binding is at equilibrium and that product release does not limit kcat
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nitroethane + H2O
ethanal + nitrite + H2O2
solvent isotope and viscositiy effects: the kcat proton inventory is consistent with a single exchangeable proton in flight, while the kcat/KM is consistent with either a single proton in flight in the transition state or a medium effect. Increasing the solvent viscosity does not affect the kcat or kcat/KM value significantly, establishing that nitroethane binding is at equilibrium and that product release does not limit kcat
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acetaldehyde + nitrite + H2O2
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nitroethane + O2
acetaldehyde + HNO2
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at pH 7, bi-ter ping-pong mechanism with oxygen reacting with the free reduced enzyme after release of the aldehyde product
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nitroethane + O2 + H2O
ethanal + nitrite + H2O2
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nitroethane is the only substrate, of diverse primary and secondary alkanes, for which deprotonation is fully rate limiting for the reductive half reaction
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nitroethane + O2 + H2O
ethanal + nitrite + H2O2
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O2 is delivered from air-saturated buffer in the assay reaction
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nitroethane + O2 + H2O
ethanal + nitrite + H2O2
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substrate CH-bond cleavage is rate limiting for the reduction of the enzyme by nitroethane
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nitroethane + O2 + H2O
ethanal + nitrite + H2O2
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the neutral substrate form is preferred, 5fold lower activity with the substrate anion, the D402 mutant enzymes in contrast prefer the anionic substrate form
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the physiological role of the enzyme is the oxidation of nitroaliphatic species
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additional information
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analysis of reaction intermediates formed by mass spectrometry and gel filtration
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additional information
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enzyme catalyzes the oxidation of nitroalkanes to the respective aldehydes or ketones with consumption of molecular oxygen and releasing nitrite and hydrogen peroxide
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additional information
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enzyme catalyzes the oxidation of primary and secondary nitroalkanes to the respective aldehydes or ketones, releasing nitrite
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additional information
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enzyme does not require anionic nitroalkanes for activity, enzyme catalyzes the oxidation of a number of primary and secondary nitroalkanes to the respective aldehydes or ketones with preference for primary nitroalkanes, monotonic increase with each additional methylene group from nitroethane to 1-nitrobutane increasing kcat/Km value by 20fold, no further increase with 1-nitropentane and 1-nitrohexane
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additional information
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enzyme shows high substrate specificity
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additional information
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the enzyme does not oxidize acyl-CoA substrates and prefers primary nitroalkanes containing four or more carbon atoms
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additional information
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slight activity, less than 5% of the activity towards nitroethane with: nitromethane, nitroacetic acid, 1-chloro-1-nitropropane, methylene blue also can function as hydrogen acceptor with low reaction rate
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additional information
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involved in the conversion of toxic nitroalkanes to less harmful compounds
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additional information
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involved in the conversion of toxic nitroalkanes to less harmful compounds
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additional information
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enzyme prefers the neutral forms of substrates and only reacts with anionic 2-nitropropane at a low rate
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additional information
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enzyme prefers the neutral forms of substrates and only reacts with anionic 2-nitropropane at a low rate
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