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1-hydroxybutyl-2-nitronate + O2
3-hydroxy-butane-2-one + HNO2
-
-
-
-
?
1-hydroxybutyl-2-nitronate + O2
? + HNO2
-
anionic, expression on the basis of the reactivity of propyl-2-nitronate with 2-nitropropane dioxygenase: 31.5
-
-
?
1-hydroxyethyl-2-nitronate + O2
glycoaldehyde + HNO2
-
-
-
-
?
1-nitrobutane + O2
? + HNO2
-
-
-
-
?
1-nitrobutane + O2
butyraldehyde + HNO2
1-nitrobutane + O2
butyraldehyde + nitrite
-
-
-
?
1-nitrohexane + O2
? + HNO2
-
-
-
-
?
1-nitrohexane + O2
hexanaldehyde + HNO2
1-nitrohexane + O2
hexanaldehyde + nitrite
-
-
-
?
1-nitropentane + O2
? + HNO2
1-nitropentane + O2
pentanaldehyde + HNO2
1-nitropentane + O2
pentanaldehyde + nitrite
-
-
-
?
1-nitropropane + O2
1,1-dinitropropane + HNO2
-
-
-
-
?
1-nitropropane + O2
? + HNO2
-
-
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
1-nitropropane + O2
propionaldehyde + nitrite
-
-
-
?
1-nitropropane + O2 + H2O
propionaldehyde + HNO2 + H2O2
-
-
-
-
?
2 Cu((CH3)2CNO2)(PPh3)2 + O2
2 Cu(O2N)(PPh3)2 + 2 propan-2-one
-
using a copper(I) aci-2-nitropropanate complex
-
-
?
2-hydroxybutyl-3-nitronate + O2
? + HNO2
-
anionic, expression on the basis of the reactivity of propyl-2-nitronate with 2-nitropropane dioxygenase: 26.7
-
-
?
2-hydroxypentyl-3-nitronate + O2
2-hydroxy-pentane-3-one + HNO2
-
-
-
-
?
2-hydroxypentyl-3-nitronate + O2
? + HNO2
-
anionic, expression on the basis of the reactivity of propyl-2-nitronate with 2-nitropropane dioxygenase: 32.3
-
-
?
2-nitro-1-butanol + O2
1-hydroxy-butane-2-one + HNO2
2-nitro-1-propanol + O2
1-hydroxy-propane-2-one + HNO2
2-nitro-1-propanol + O2
? + HNO2
-
-
-
-
?
2-nitro-1H-indene-1,3(2H)-dione + Cu(0) + N,N,N',N'-tetramethylethylenediamine + O2
1H-indene-1,2,3,-trione + (NO2)CuN,N,N',N'-tetramethylethylenediamine
-
with N,N-dimethylformamid (conversion: 30%) as solvent
-
-
?
2-nitroethanol + O2
? + HNO2
-
-
-
-
?
2-nitroethanol + O2
glycoaldehyde + HNO2
-
13% of the activity with 2-nitropropane
-
-
?
2-nitroethanol + O2 + H2O
? + HNO2 + H2O2
-
8.4% relative activity (1-nitropropane: 100%)
-
-
?
2-nitropropane + O2
?
-
-
-
?
2-nitropropane + O2
? + HNO2
-
-
-
-
?
2-nitropropane + O2
acetone + HNO2
2-nitropropane + O2
acetone + nitrite
-
-
-
?
2-nitropropane + O2 + H2O
acetone + HNO2 + H2O2
-
96.9% relative activity (1-nitropropane: 100%)
-
-
?
3 propionate-3-nitronate + O2
3 malonic semialdehyde + nitrite + 2 nitrate + H2O2
3-nitro-1-butanol + O2 + H2O
? + HNO2 + H2O2
-
15.7% relative activity (1-nitropropane: 100%)
-
-
?
3-nitro-2-butanol + O2
3-hydroxy-butane-2-one + HNO2
3-nitro-2-butanol + O2
? + HNO2
-
-
-
-
?
3-nitro-2-butanol + O2 + H2O
? + HNO2 + H2O2
-
6.5% relative activity (1-nitropropane: 100%)
-
-
?
3-nitro-2-pentanol + O2
2-hydroxy-pentane-3-one + HNO2
3-nitro-2-pentanol + O2
? + HNO2
-
-
-
-
?
3-nitro-2-pentanol + O2 + H2O
2-hydroxy-pentane-3-one + HNO2 + H2O2
-
116% relative activity (1-nitropropane: 100%)
-
-
?
3-nitropropionate + O2
?
-
-
-
-
?
3-nitropropionate + O2 + H2O
? + HNO2 + H2O2
-
0.5% relative activity (1-nitropropane: 100%)
-
-
?
3-nitropropionic acid + O2
?
butyl-1-nitronate + O2
?
-
-
-
?
butyl-1-nitronate + O2
? + nitrite
butyl-1-nitronate + O2
NO2- + butanal
-
-
-
?
cyclohexyl nitronate + O2
? + HNO2
-
-
-
-
?
ethyl nitronate + O2
? + nitrite
ethyl nitronate + O2
acetaldehyde + HNO2
-
-
-
-
?
ethylnitronate + Cu(0) + N,N,N',N'-tetramethylethylenediamine + O2
acetone + (NO2)CuN,N,N',N'-tetramethylethylenediamine
-
with N,N-dimethylformamid (conversion: 60%) and pyridine (conversion: 90%) as solvent
-
-
?
ethylnitronate + O2
acetaldehyde + HNO2
ethylnitronate + O2
acetaldehyde + nitrite + other products
-
-
-
?
ethylnitronate + O2
NO2- + acetaldehyde
-
-
-
?
ethylnitronate + O2 + FMNH2
acetaldehyde + nitrite + FMN + H2O
hexyl-1-nitronate + O2
? + nitrite
hexyl-1-nitronate + O2
NO2- + hexanal
-
-
-
?
nitrocyclohexane + O2
? + HNO2
nitrocyclohexane + O2
cyclohexanone + HNO2
nitrocyclohexane + O2 + H2O
cyclohexanone + HNO2 + H2O2
-
99.8% relative activity (1-nitropropane: 100%)
-
-
?
nitrocyclopentane + O2
? + HNO2
-
-
-
-
?
nitroethane + O2
? + nitrite
-
-
-
-
?
nitroethane + O2
acetaldehyde + HNO2
nitroethane + O2
acetaldehyde + HNO2 + 1,1-dinitroethane
-
in contrast with the unambiguous stoichiometry of 2-nitropropane oxidation, the nitroethane oxidation is stoichiometrically complicated; 1,1-dinitroethane and nitrate are formed as minor products
-
-
?
nitroethane + O2
acetaldehyde + nitrite
nitroethane + O2
ethanal + nitrite
nitroethane + O2
ethylnitronate
-
2-nitropropane dioxygenase utilizes a branched catalytic mechanism with nitroethane as substrate. The branch point occurs at the enzyme-ethylnitronate complex and involves either the release of the nitronate or an oxidative denitrification reaction. The partitioning of the enzyme-nitronate complex results in the formation of multiple products from independent catalytic pathways with nitroethane as substrate for the enzyme. In the nonoxidative pathway, nitroethane is deprotonated by histidine 196 to generate ethylnitronate which is subsequently released from the enzyme as a reaction product. The oxidative denitrification pathway was established in previous studies of the enzyme and involves the oxidation of ethylnitronate by the enzyme bound flavin to generate acetaldehyde and nitrite as product
-
-
r
nitroethane + O2 + H2O
? + HNO2 + H2O2
-
51.8% relative activity (1-nitropropane: 100%)
-
-
?
nitroethane + O2 + H2O
ethanal + nitrite + H2O2
nitromethane + O2
? + HNO2
-
-
-
-
?
nitromethane + O2
formaldehyde + HNO2
nitromethane + O2 + H2O
? + HNO2 + H2O2
-
7.3% relative activity (1-nitropropane: 100%)
-
-
?
pentane-1-nitronate + Cu(0) + N,N,N',N'-tetramethylethylenediamine + O2
pentaldehyde + (NO2)CuN,N,N',N'-tetramethylethylenediamine
-
with N,N-dimethylformamid (conversion: 28%) and pyridine (conversion: 21%) as solvent
-
-
?
pentyl-1-nitronate + O2
?
-
-
-
?
pentyl-1-nitronate + O2
? + HNO2
-
-
-
-
?
pentyl-1-nitronate + O2
? + nitrite
pentyl-1-nitronate + O2
NO2- + pentanal
-
-
-
?
propionate 3-nitronate + O2
?
-
-
-
-
?
propionate-3-nitronate + O2
?
propyl-1-nitronate + O2
?
propyl-1-nitronate + O2
? + nitrite
propyl-1-nitronate + O2
NO2- + propionaldehyde
-
-
-
?
propyl-1-nitronate + O2
propionaldehyde + HNO2
-
-
-
-
?
propyl-1-nitronate + O2 + FMNH2
? + nitrite + FMN + H2O
-
-
-
-
?
propyl-2-nitronate + Cu(0) + 1,10-phenanthroline + O2
propan-2-one + ?
-
with methanol (conversion: 42%), MeCN (conversion: 24%), and N,N-dimethylformamid (conversion: 43%)
-
-
?
propyl-2-nitronate + Cu(0) + 2,2'-bipyridine + O2
propan-2-one + ?
-
with methanol (conversion: 44%), MeCN (conversion: 54%), and N,N-dimethylformamid (conversion: 37%)
-
-
?
propyl-2-nitronate + Cu(0) + N,N,N',N'-tetramethylethylenediamine + O2
propan-2-one + (NO2)CuN,N,N',N'-tetramethylethylenediamine
-
with methanol (conversion: 70%), MeCN (conversion: 49%), N,N-dimethylformamid (conversion: 71%), and pyridine (conversion: 67%) as solvent
-
-
?
propyl-2-nitronate + Cu(0) + O2
propan-2-one + ?
-
without ligand and without solvent (conversion: 12%)
-
-
?
propyl-2-nitronate + O2
?
-
-
-
?
propyl-2-nitronate + O2
? + nitrite
propyl-2-nitronate + O2
acetone + HNO2
propyl-2-nitronate + O2
NO2- + acetone
-
-
-
?
propyl-2-nitronate + O2 + FMNH2
? + nitrite + FMN + H2O
propylnitronate + O2
? + HNO2
-
anionic, expression on the basis of the reactivity of propyl-2-nitronate with 2-nitropropane dioxygenase: 57.9
-
-
?
undecan-6-nitronate + Cu(0) + N,N,N',N'-tetramethylethylenediamine + O2
undecan-6-one + (NO2)CuN,N,N',N'-tetramethylethylenediamine
-
with N,N-dimethylformamid (conversion: 66%) and pyridine (conversion: 67%) as solvent
-
-
?
additional information
?
-
1-nitrobutane + O2

butyraldehyde + HNO2
-
-
-
?
1-nitrobutane + O2
butyraldehyde + HNO2
neutral and anionic form
-
-
?
1-nitrohexane + O2

hexanaldehyde + HNO2
-
-
-
?
1-nitrohexane + O2
hexanaldehyde + HNO2
neutral and anionic form
-
-
?
1-nitropentane + O2

? + HNO2
-
-
-
-
?
1-nitropentane + O2
? + HNO2
-
3% of the activity with 2-nitropropane
-
-
?
1-nitropentane + O2

pentanaldehyde + HNO2
-
-
-
?
1-nitropentane + O2
pentanaldehyde + HNO2
neutral and anionic form
-
-
?
1-nitropropane + O2

propionaldehyde + HNO2
-
-
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
57.9% of activity with 2-nitropropane
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
-
23.4% of the activity with 2-nitropropane
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
57.9% of activity with 2-nitropropane (anionic form)
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
-
23.4% of the activity with 2-nitropropane
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
-
-
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
-
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
-
21% of the activity with 2-nitropropane
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
neutral and anionic form
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
-
-
-
?
2-nitro-1-butanol + O2

1-hydroxy-butane-2-one + HNO2
31.5% of the activity with 2-nitropropane
-
-
?
2-nitro-1-butanol + O2
1-hydroxy-butane-2-one + HNO2
2.7% of the activity with 2-nitropropane
-
-
?
2-nitro-1-butanol + O2
1-hydroxy-butane-2-one + HNO2
2.7% of the activity with 2-nitropropane (anionic form)
-
-
?
2-nitro-1-butanol + O2
1-hydroxy-butane-2-one + HNO2
31.5% of the activity with 2-nitropropane (anionic form)
-
-
?
2-nitro-1-propanol + O2

1-hydroxy-propane-2-one + HNO2
7.7% of activity with 2-nitropropane
-
-
?
2-nitro-1-propanol + O2
1-hydroxy-propane-2-one + HNO2
7.7% of activity with 2-nitropropane (anionic form)
-
-
?
2-nitropropane + O2

acetone + HNO2
-
-
-
?
2-nitropropane + O2
acetone + HNO2
-
-
-
?
2-nitropropane + O2
acetone + HNO2
-
-
-
-
?
2-nitropropane + O2
acetone + HNO2
-
superoxide as reactive intermediate
-
-
?
2-nitropropane + O2
acetone + HNO2
-
-
-
?
2-nitropropane + O2
acetone + HNO2
-
superoxide as reactive intermediate
-
-
?
2-nitropropane + O2
acetone + HNO2
-
-
-
-
?
2-nitropropane + O2
acetone + HNO2
-
-
-
-
?
2-nitropropane + O2
acetone + HNO2
-
-
-
-
?
2-nitropropane + O2
acetone + HNO2
-
-
-
?
2-nitropropane + O2
acetone + HNO2
neutral and anionic form
-
-
?
2-nitropropane + O2
acetone + HNO2
-
-
-
?
2-nitropropane + O2
acetone + HNO2
anionic form
-
-
?
2-nitropropane + O2
acetone + HNO2
-
-
-
?
3 propionate-3-nitronate + O2

3 malonic semialdehyde + nitrite + 2 nitrate + H2O2
-
-
-
?
3 propionate-3-nitronate + O2
3 malonic semialdehyde + nitrite + 2 nitrate + H2O2
best substrate
-
-
?
3-nitro-2-butanol + O2

3-hydroxy-butane-2-one + HNO2
26.7% of the activity with 2-nitropropane
-
-
?
3-nitro-2-butanol + O2
3-hydroxy-butane-2-one + HNO2
-
13% of the activity with 2-nitropropane
-
-
?
3-nitro-2-butanol + O2
3-hydroxy-butane-2-one + HNO2
-
slight oxidation
-
-
?
3-nitro-2-butanol + O2
3-hydroxy-butane-2-one + HNO2
26.7% of the activity with 2-nitropropane (anionic form)
-
-
?
3-nitro-2-butanol + O2
3-hydroxy-butane-2-one + HNO2
-
14% of the activity with 2-nitropropane
-
-
?
3-nitro-2-pentanol + O2

2-hydroxy-pentane-3-one + HNO2
32.3% of the activity with 2-nitropropane
-
-
?
3-nitro-2-pentanol + O2
2-hydroxy-pentane-3-one + HNO2
-
40.6% of the activity with 2-nitropropane
-
-
?
3-nitro-2-pentanol + O2
2-hydroxy-pentane-3-one + HNO2
32.3% of the activity with 2-nitropropane (anionic form)
-
-
?
3-nitro-2-pentanol + O2
2-hydroxy-pentane-3-one + HNO2
-
-
-
-
?
3-nitro-2-pentanol + O2
2-hydroxy-pentane-3-one + HNO2
-
20% of the activity with 2-nitropropane
-
-
?
3-nitropropionic acid + O2

?
25.5% of the activity with 2-nitropropane
-
-
?
3-nitropropionic acid + O2
?
-
11.7% of the activity with 2-nitropropane
-
-
?
3-nitropropionic acid + O2
?
25.5% of the activity with 2-nitropropane (anionic form)
-
-
?
3-nitropropionic acid + O2
?
-
12% of the activity with 2-nitropropane
-
-
?
butyl-1-nitronate + O2

? + nitrite
-
-
-
?
butyl-1-nitronate + O2
? + nitrite
neutral and anionic form
-
-
?
ethyl nitronate + O2

? + nitrite
-
-
-
-
?
ethyl nitronate + O2
? + nitrite
-
-
-
-
?
ethyl nitronate + O2
? + nitrite
-
-
-
?
ethyl nitronate + O2
? + nitrite
-
anionic form of the substrate
-
-
?
ethylnitronate + O2

acetaldehyde + HNO2
-
anionic, expression on the basis of the reactivity of propyl-2-nitronate with 2-nitropropane dioxygenase: 32.5
-
-
?
ethylnitronate + O2
acetaldehyde + HNO2
neutral and anionic form
-
-
?
ethylnitronate + O2 + FMNH2

acetaldehyde + nitrite + FMN + H2O
-
-
-
-
?
ethylnitronate + O2 + FMNH2
acetaldehyde + nitrite + FMN + H2O
-
-
-
-
?
ethylnitronate + O2 + FMNH2
acetaldehyde + nitrite + FMN + H2O
-
-
-
-
?
ethylnitronate + O2 + FMNH2
acetaldehyde + nitrite + FMN + H2O
-
reaction via ethylnitronate radical. Catalytic turnover of NMO with ethylnitronate as substrate occurs through both an oxidative denitrification pathway and a non-oxidative pathway in which the anionic substrate is protonated in the active site of the enzyme to form nitroethane as a reaction product
-
-
?
ethylnitronate + O2 + FMNH2
acetaldehyde + nitrite + FMN + H2O
-
-
-
?
hexyl-1-nitronate + O2

? + nitrite
-
-
-
?
hexyl-1-nitronate + O2
? + nitrite
neutral and anionic form
-
-
?
nitrocyclohexane + O2

? + HNO2
-
-
-
-
?
nitrocyclohexane + O2
? + HNO2
-
2% of the activity with 2-nitropropane
-
-
?
nitrocyclohexane + O2

cyclohexanone + HNO2
1.5% of the activity with 2-nitropropane
-
-
?
nitrocyclohexane + O2
cyclohexanone + HNO2
1.5% of the activity with 2-nitropropane (anionic form)
-
-
?
nitrocyclohexane + O2
cyclohexanone + HNO2
-
-
-
-
?
nitroethane + O2

acetaldehyde + HNO2
-
-
-
-
?
nitroethane + O2
acetaldehyde + HNO2
4.2% of the activity with 2-nitropropane
-
-
?
nitroethane + O2
acetaldehyde + HNO2
-
88% of the activity with nitroethane
-
?
nitroethane + O2
acetaldehyde + HNO2
-
formation of 1,1-dinitroethane and nitrate as minor products
-
-
?
nitroethane + O2
acetaldehyde + HNO2
4.2% of the activity with 2-nitropropane (anionic form)
-
-
?
nitroethane + O2
acetaldehyde + HNO2
-
88% of the activity with nitroethane
-
-
?
nitroethane + O2
acetaldehyde + HNO2
-
-
-
-
?
nitroethane + O2
acetaldehyde + HNO2
-
27% of the activity with 2-nitropropane
-
-
?
nitroethane + O2
acetaldehyde + HNO2
-
neutral form of the substrate
-
-
?
nitroethane + O2
acetaldehyde + HNO2
-
The kinetic isotope effect on the second-order rate constant for nitronate formation, kcat/Km, decreases from an upper limiting value of 23 at low pH to a lower limiting value of 11 at high pH. The difference in the kinetic isotope effects arises from the branching of an enzyme-ethylnitronate reaction intermediate through oxidative and nonoxidative turnover. This branching is isotope sensitive due to a kinetic isotope effect on nitronate release rather than on flavin reduction. The kinetic isotope effect on ethylnitronate release arises from the deprotonation of histidine 196, which provides electrostatic interactions with the nitronate to keep it bound in the active site for oxidation. The isotope effect on branching results in an inflation of the kinetic isotope observed for the nonoxidative pathway to values that are larger than the intrinsic values associated with C-H bond cleavage
-
-
?
nitroethane + O2
acetaldehyde + HNO2
-
-
-
?
nitroethane + O2

acetaldehyde + nitrite
-
-
-
-
?
nitroethane + O2
acetaldehyde + nitrite
-
2-nitropropane dioxygenase utilizes a branched catalytic mechanism with nitroethane as substrate. The branch point occurs at the enzyme-ethylnitronate complex and involves either the release of the nitronate or an oxidative denitrification reaction. The partitioning of the enzyme-nitronate complex results in the formation of multiple products from independent catalytic pathways with nitroethane as substrate for the enzyme. In the nonoxidative pathway, nitroethane is deprotonated by histidine 196 to generate ethylnitronate which is subsequently released from the enzyme as a reaction product. The oxidative denitrification pathway was established in previous studies of the enzyme and involves the oxidation of ethylnitronate by the enzyme bound flavin to generate acetaldehyde and nitrite as product
-
-
?
nitroethane + O2
acetaldehyde + nitrite
-
catalytic turnover of NMO with nitroethane as substrate occurs with oxidative and non-oxidative pathways with ethylnitronate formation and release in assays of the enzyme with the neutral substrate. The nonoxidative pathway of the enzyme with nitroethane as substrate also involves the H196-catalyzed deprotonation of the nitroalkane and the release of ethylnitronate as a reaction product
-
-
?
nitroethane + O2
acetaldehyde + nitrite
-
-
-
?
nitroethane + O2

ethanal + nitrite
-
-
-
?
nitroethane + O2
ethanal + nitrite
neutral and anionic form
-
-
?
nitroethane + O2 + H2O

ethanal + nitrite + H2O2
-
-
-
-
?
nitroethane + O2 + H2O
ethanal + nitrite + H2O2
-
-
-
?
nitromethane + O2

formaldehyde + HNO2
-
no activity
-
-
?
nitromethane + O2
formaldehyde + HNO2
4.2% of the activity with 2-nitropropane activity
-
-
?
nitromethane + O2
formaldehyde + HNO2
4.2% of the activity with 2-nitropropane activity (anionic form)
-
-
?
nitromethane + O2
formaldehyde + HNO2
-
is not a substrate, under anaerobic conditions. The aerobic dialysis of the enzyme treated with nitromethane causes reoxidation of only the Fe2+
-
-
?
pentyl-1-nitronate + O2

? + nitrite
-
-
-
?
pentyl-1-nitronate + O2
? + nitrite
neutral and anionic form
-
-
?
propionate-3-nitronate + O2

?
-
-
-
-
?
propionate-3-nitronate + O2
?
-
-
-
-
?
propyl-1-nitronate + O2

?
-
-
-
?
propyl-1-nitronate + O2
?
-
-
-
?
propyl-1-nitronate + O2

? + nitrite
-
-
-
?
propyl-1-nitronate + O2
? + nitrite
neutral and anionic form
-
-
?
propyl-2-nitronate + O2

? + nitrite
-
-
-
?
propyl-2-nitronate + O2
? + nitrite
neutral and anionic form
-
-
?
propyl-2-nitronate + O2

acetone + HNO2
-
anionic
-
-
?
propyl-2-nitronate + O2
acetone + HNO2
-
-
-
-
?
propyl-2-nitronate + O2 + FMNH2

? + nitrite + FMN + H2O
-
-
-
-
?
propyl-2-nitronate + O2 + FMNH2
? + nitrite + FMN + H2O
-
-
-
-
?
propyl-2-nitronate + O2 + FMNH2
? + nitrite + FMN + H2O
-
-
-
-
?
additional information

?
-
anaerobic substrate reduction and kinetic data using a Clark oxygen electrode to measure rates of oxygen consumption indicated that the enzyme is active on a broad range of alkyl nitronates, with a marked preference for unbranched substrates over propyl-2-nitronate. The enzyme utilizes alkyl nitronates for catalysis, but not nitroalkanes
-
-
?
additional information
?
-
-
anaerobic substrate reduction and kinetic data using a Clark oxygen electrode to measure rates of oxygen consumption indicated that the enzyme is active on a broad range of alkyl nitronates, with a marked preference for unbranched substrates over propyl-2-nitronate. The enzyme utilizes alkyl nitronates for catalysis, but not nitroalkanes
-
-
?
additional information
?
-
-
enzyme catalyzes the oxygenative denitrification of anionic nitroalkanes much more effectively than that of the neutral ones
-
-
?
additional information
?
-
enzyme catalyzes the oxygenative denitrification of anionic nitroalkanes much more effectively than that of the neutral ones
-
-
?
additional information
?
-
anaerobic substrate reduction and kinetic data using a Clark oxygen electrode to measure rates of oxygen consumption indicates that the enzyme is active on a broad range of alkyl nitronates, with a marked preference for unbranched substrates over propyl-2-nitronate. The enzyme utilizes alkyl nitronates for catalysis, but not nitroalkanes
-
-
?
additional information
?
-
-
anaerobic substrate reduction and kinetic data using a Clark oxygen electrode to measure rates of oxygen consumption indicates that the enzyme is active on a broad range of alkyl nitronates, with a marked preference for unbranched substrates over propyl-2-nitronate. The enzyme utilizes alkyl nitronates for catalysis, but not nitroalkanes
-
-
?
additional information
?
-
-
no activity, nitromethane is inert to the enzyme. The nitroalkanes are not oxidized under anaerobic conditions
-
-
?
additional information
?
-
-
sodium dithionite also reduces both the enzyme-bound FAD and Fe3+ under anaerobic conditions
-
-
?
additional information
?
-
-
sodium dithionite also reduces both the enzyme-bound FAD and Fe3+ under anaerobic conditions
-
-
?
additional information
?
-
-
only alkyl nitronates are used as substrates in the oxidative denitrification reaction catalyzed by Williopsis saturnus var. mrakii NMO, nitroalkanes are no substrates. The different substrate specificity compared to other NMOs might result from the presence of a His residue in the active site and conformational differences. NMO does not produce and release hydrogen peroxide during turnover with linear alkyl nitronates of various lengths between 2 and 6 carbon atoms or with propyl-2-nitronate. With the exception of propyl-2-nitronate, there is no release of superoxide during turnover of NMO at pH 8.0 and 30°C with linear alkyl nitronates with chain lengths between 2 and 6 carbon atoms
-
-
?
additional information
?
-
-
only alkyl nitronates are used as substrates in the oxidative denitrification reaction catalyzed by Williopsis saturnus var. mrakii NMO, nitroalkanes are no substrates. The different substrate specificity compared to other NMOs might result from the presence of a His residue in the active site and conformational differences. NMO does not produce and release hydrogen peroxide during turnover with linear alkyl nitronates of various lengths between 2 and 6 carbon atoms or with propyl-2-nitronate. With the exception of propyl-2-nitronate, there is no release of superoxide during turnover of NMO at pH 8.0 and 30°C with linear alkyl nitronates with chain lengths between 2 and 6 carbon atoms
-
-
?
additional information
?
-
-
active on primary and secondary nitroalkanes, with a marked preference for unbranched primary nitroalkanes
-
-
?
additional information
?
-
-
anionic forms of nitroalkanes are much better substrates than are neutral forms, enzyme does not act on aromatic compounds
-
-
?
additional information
?
-
the reduced enzyme can reduce the substrate under anaerobically conditions, substrate specificity with nitroalkanes and alkyl nitronates, O2 is delivered from air-saturated buffer in the assay reaction, enzyme catalyzes the 2-step oxidative denitrification of nitroalkanes to their corresponding carbonyl compounds and nitrite
-
-
?
additional information
?
-
-
the reduced enzyme can reduce the substrate under anaerobically conditions, substrate specificity with nitroalkanes and alkyl nitronates, O2 is delivered from air-saturated buffer in the assay reaction, enzyme catalyzes the 2-step oxidative denitrification of nitroalkanes to their corresponding carbonyl compounds and nitrite
-
-
?
additional information
?
-
enzyme is more specific for nitronates than nitroalkanes
-
-
?
additional information
?
-
-
enzyme is more specific for nitronates than nitroalkanes
-
-
?
additional information
?
-
-
2-nitropropane dioxygenase utilizes a branched catalytic mechanism with nitroethane as substrate. The branch point occurs at the enzyme-ethylnitronate complex and involves either the release of the nitronate or an oxidative denitrification reaction. The partitioning of the enzyme-nitronate complex results in the formation of multiple products from independent catalytic pathways with nitroethane as substrate for the enzyme. In the nonoxidative pathway, nitroethane is deprotonated by histidine 196 to generate ethylnitronate which is subsequently released from the enzyme as a reaction product
-
-
?
additional information
?
-
-
anionic forms of nitroalkanes are much better substrates than are neutral forms, enzyme does not act on aromatic compounds. Measuring nitrite production with 20 mM anionic nitro compounds as substrates
-
-
?
additional information
?
-
-
both the neutral and anionic forms of nitroalkanes act as substrates for the oxidative denitrification reaction catalyzed by Neurospora crassa NMO. NMO does not produce and release hydrogen peroxide during turnover with linear alkyl nitronates of various lengths between 2 and 6 carbon atoms or with propyl-2-nitronate. With the exception of propyl-1- and propyl-2-nitronate, there is no release of superoxide during turnover of NMO at pH 8.0 and 30°C with linear alkyl nitronates with chain lengths between 2 and 6 carbon atoms
-
-
?
additional information
?
-
the enzyme is active on propionate-3-nitronate and other alkyl nitronates, but cannot oxidize nitroalkanes, e.g. 3-nitropropionate, nitroethane, 1-nitropropane, 1-nitrobutane, 1-nitropentane, or 2-nitropropane. Anaerobic reduction of the enzyme with propionate-3-nitronate yields a flavosemiquinone
-
-
?
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1.4
1-nitrohexane
in 50 mM Tris-HCl, pH 8 at 30°C
7.1
1-nitropentane
in 50 mM Tris-HCl, pH 8 at 30°C
0.59 - 4.2
3-Nitro-2-butanol
1.04 - 6.8
3-Nitro-2-pentanol
0.58
3-nitropropionate
-
pH 7.4, 30°C
10
butyl-1-nitronate
in 50 mM Tris-HCl, pH 8 at 30°C
1.4
hexyl-1-nitronate
in 50 mM Tris-HCl, pH 8 at 30°C
0.06
propionate 3-nitronate
-
pH 5.5, 30°C
0.11 - 0.34
propionate-3-nitronate
5.5 - 8.3
propyl-1-nitronate
1.61 - 3.1
propyl-2-nitronate
additional information
additional information
-
15
1-nitrobutane

in 50 mM Tris-Cl, pH 8 at 30°C
17.9
1-nitrobutane
in 50 mM Tris-HCl, pH 8 at 30°C
1.54
1-Nitropropane

-
-
3.23
1-Nitropropane
anionic form of substrate
3.23
1-Nitropropane
anionic form of the substrate
8.3
1-Nitropropane
-
anionic form of substrate
20
1-Nitropropane
-
neutral form of substrate
24
1-Nitropropane
in 50 mM Tris-HCl, pH 8 at 30°C
25.6
1-Nitropropane
neutral form of substrate
25.6
1-Nitropropane
neutral form of the substrate
1.61
2-Nitropropane

anionic form of substrate
1.61
2-Nitropropane
-
anionic form of substrate
1.61
2-Nitropropane
anionic form of the substrate
3.1
2-Nitropropane
-
anionic form of substrate
6
2-Nitropropane
-
anionic form of substrate
21.3
2-Nitropropane
neutral form of substrate
21.3
2-Nitropropane
neutral form of the substrate
33
2-Nitropropane
-
neutral form of substrate
0.59
3-Nitro-2-butanol

anionic form of substrate
0.59
3-Nitro-2-butanol
anionic form of the substrate
4.2
3-Nitro-2-butanol
-
neutral form of substrate
4.2
3-Nitro-2-butanol
neutral form of the substrate
1.04
3-Nitro-2-pentanol

anionic form of substrate
1.04
3-Nitro-2-pentanol
anionic form of the substrate
3.08
3-Nitro-2-pentanol
-
-
6.8
3-Nitro-2-pentanol
-
-
3.1
ethyl nitronate

in 50 mM Tris-HCl, pH 8 at 30°C
3.4
ethyl nitronate
-
at pH 8.0 and 30°C
4
ethyl nitronate
-
pH 8, 30°C
4
ethyl nitronate
-
pH 6, 30°C
5.1
ethyl nitronate
-
at pH 6.0 and 30°C
6
ethyl nitronate
-
anionic form of substrate
9.5
ethyl nitronate
-
at pH 9.0 and 30°C
10
ethyl nitronate
-
pH 11, 30°C
20
ethyl nitronate
-
pH 5.5, 30°C
5
ethylnitronate

pH 7.5, 30°C, recombinant enzyme
11
ethylnitronate
-
30°C, pH 9.5, mutant enzyme H196N
15.9
ethylnitronate
-
30°C, pH 9.5, wild-type enzyme
1
nitroethane

-
-
2 - 3
nitroethane
-
neutral form of substrate
3.13
nitroethane
anionic form of substrate
3.13
nitroethane
anionic form of the substrate
6.8
nitroethane
neutral form of substrate
6.8
nitroethane
neutral form of the substrate
13
nitroethane
-
at pH 9.0 and 30°C
19
nitroethane
-
at pH 8.0 and 30°C
23
nitroethane
-
neutral form of substrate
24.3
nitroethane
neutral form of substrate
24.3
nitroethane
neutral form of the substrate
29
nitroethane
in 50 mM Tris-HCl, pH 8 at 30°C
0.005
O2

-
with ethyl nitronate at pH 8.0 and 30°C
0.005
O2
-
with nitroethane at pH 9.0 and 30°C
0.005
O2
-
30°C, pH 8, wild-type enzyme, ethylnitronate as a substrate
0.005
O2
-
with ethyl nitronate at pH 8.0 and 30°C; with nitroethane at pH 9.0 and 30°C
0.01
O2
-
with nitroethane at pH 6.0 and 30°C
0.02
O2
-
with either ethyl nitronate or nitroethane at pH 6.0 and 30°C
0.034
O2
-
30°C, pH 8, mutant enzyme H196N
0.034
O2
-
30°C, pH 8, mutant enzyme H196N, ethylnitronate as a substrate
0.045
O2
-
with ethyl nitronate at pH 9.0 and 30°C
0.11
propionate-3-nitronate

pH 7.5, 30°C, recombinant enzyme
0.27
propionate-3-nitronate
-
pH 7.4, 30°C
0.34
propionate-3-nitronate
-
pH 7.4, 30°C
5.5
propyl-1-nitronate

in 50 mM Tris-HCl, pH 8 at 30°C
6
propyl-1-nitronate
pH 7.5, 30°C, recombinant enzyme
8.3
propyl-1-nitronate
-
anionic form of substrate
1.61
propyl-2-nitronate

-
anionic
3.1
propyl-2-nitronate
-
anionic form of substrate
additional information
additional information

kinetics, steady-state kinetic mechanism
-
additional information
additional information
-
kinetics, steady-state kinetic mechanism
-
additional information
additional information
-
Km-value for O2 (wild-type enzyme) is below 0.005 mM
-
additional information
additional information
-
steady-state kinetic mechanism with ethylnitronate, overview
-
additional information
additional information
steady-state kinetic mechanism
-
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2-Nitropropane dioxygenase from Hansenula mrakii: re-characterization of the enzyme and oxidation of anionic nitroalkanes
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48
2549-2554
1984
Cyberlindnera mrakii, Cyberlindnera mrakii (Q12723)
-
brenda
Kido, T.; Soda, K.; Suzuki, T.; Asada, K.
A new oxygenase, 2-nitropropane dioxygenase of Hansenula mrakii. Enzymologic and spectrophotometric properties
J. Biol. Chem.
251
6994-7000
1976
Cyberlindnera mrakii, Cyberlindnera mrakii IF0 0895
brenda
Kido, T.; Soda, K.; Asada, K.
Properties of 2-nitropropane dioxygenase of Hansenula mrakii. Formation and participation of superoxide
J. Biol. Chem.
253
226-232
1978
Cyberlindnera mrakii, Cyberlindnera mrakii IF0 0895
brenda
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Purification and properties of nitroalkane oxidase from Fusarium oxysporum
J. Bacteriol.
133
53-58
1978
Fusarium oxysporum
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Characterization of primary nitroalkane oxidation by 2-nitropropane dioxygenase
Agric. Biol. Chem.
48
1361-1362
1984
Cyberlindnera mrakii
-
brenda
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Oxidation of anionic nitroalkanes by flavoenzymes, and participation of superoxide anion in the catalysis
Arch. Biochem. Biophys.
234
468-475
1984
Cyberlindnera mrakii
brenda
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Purification, characterization, and mechanism of a flavin mononucleotide-dependent 2-nitropropane dioxygenase from Neurospora crassa
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Substrate specificity of a nitroalkane-oxidizing enzyme
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363
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1999
Fusarium oxysporum
brenda
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Purification and properties of nitroalkane-oxidizing enzyme from Hansenula mrakii
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280
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Probing the chemical steps of nitroalkane oxidation catalyzed by 2-nitropropane dioxygenase with solvent viscosity, pH, and substrate kinetic isotope effects
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45
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Neurospora crassa
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Crystal structure of 2-nitropropane dioxygenase complexed with FMN and substrate. Identification of the catalytic base
J. Biol. Chem.
281
18660-18667
2006
Pseudomonas aeruginosa (Q9I4V0), Pseudomonas aeruginosa
brenda
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Oxidation of alkyl nitronates catalyzed by 2-nitropropane dioxygenase from Hansenula mrakii
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473
61-68
2008
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brenda
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The nonoxidative conversion of nitroethane to ethylnitronate in Neurospora crassa 2-nitropropane dioxygenase is catalyzed by Histidine 196
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47
9136-9144
2008
Neurospora crassa
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Nitronate monooxygenase, a model for anionic flavin semiquinone intermediates in oxidative catalysis
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493
53-61
2009
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Inflated kinetic isotope effects in the branched mechanism of Neurospora crassa 2-nitropropane dioxygenase
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48
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Copper mediated conversion of nitro compounds to aldehydes or ketones by dioxygen
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25
573-574
1996
Cyberlindnera mrakii
-
brenda
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Copper-mediated oxygenation of nitronate to nitrite and acetone in a copper(I) nitronate complex
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37
6535-6537
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Crystal structure and site-directed mutagenesis of a nitroalkane oxidase from Streptomyces ansochromogenes
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405
344-348
2011
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A novel activity for fungal nitronate monooxygenase: detoxification of the metabolic inhibitor propionate-3-nitronate
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521
84-89
2012
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brenda
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Evidence for a transient peroxynitro acid in the reaction catalyzed by nitronate monooxygenase with propionate 3-nitronate
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52
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Rv1894c is a novel hypoxia-induced nitronate monooxygenase required for Mycobacterium tuberculosis virulence
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207
1525-1534
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Pseudomonas aeruginosa LysR PA4203 regulator NmoR acts as a repressor of the PA4202 nmoA gene, encoding a nitronate monooxygenase
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197
1026-1039
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289
23764-23775
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brenda