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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 butyl-1-nitronate + O2
2 butanal + 2 nitrite
-
-
-
-
?
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 ethylnitronate + O2
2 ethanal + 2 nitrite
-
-
-
-
?
2 propyl-1-nitronate + O2
2 propanal + 2 nitrite
-
-
-
-
?
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 + H2O
? + HNO2 + H2O2
-
0.5% relative activity (1-nitropropane: 100%)
-
-
?
3-nitropropionic acid + O2
?
butyl 1-nitronate + O2
?
-
-
-
?
butyl-1-nitronate + O2
?
-
-
-
?
butyl-1-nitronate + O2
? + nitrite
butyl-1-nitronate + O2
NO2- + butanal
-
-
-
?
cyclohexyl nitronate + O2
? + HNO2
-
-
-
-
?
ethyl nitronate + O2
?
-
-
-
?
ethyl nitronate + O2
? + nitrite
ethyl nitronate + O2
acetaldehyde + HNO2
-
-
-
-
?
ethyl nitronate + O2
ethanal + nitrite
-
-
-
-
?
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
?
-
-
-
?
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
?
-
-
-
?
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
?
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-nitroethane + O2
?
-
-
-
?
1-nitroethane + O2
?
-
-
-
?
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
?
-
-
-
?
1-nitropropane + O2
?
-
-
-
?
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
-
-
-
?
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
-
-
-
-
?
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-nitropropionate + O2
?
-
-
-
-
?
3-nitropropionate + O2
?
-
-
-
?
3-nitropropionate + O2
?
-
-
-
?
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
?
-
-
-
-
?
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
?
-
-
-
?
nitroethane + O2
?
-
-
-
?
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
?
-
-
-
-
?
propionate 3-nitronate + O2
?
-
-
-
?
propionate-3-nitronate + O2
?
-
-
-
-
?
propionate-3-nitronate + O2
?
-
-
-
-
?
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
?
-
-
kinetic evidence for an anion binding pocket in the active site of nitronate monooxygenase
-
-
?
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
?
-
-
kinetic evidence for an anion binding pocket in the active site of nitronate monooxygenase
-
-
?
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 can catalyze the oxidation of neutral or anionic nitroalkanes and alkyl nitronates to their corresponding carbonyl and nitro compounds
-
-
-
additional information
?
-
the enzyme can catalyze the oxidation of neutral or anionic nitroalkanes and alkyl nitronates to their corresponding carbonyl and nitro compounds
-
-
-
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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3-(3,4-dihydroxyphenyl)-L-Ala
-
-
3-nitro-1-propionate
-
competitive inhibitor, pH 7.0, 30°C
4-hydroxy-2,2,6,6-tetramethyl-piperidinooxy radical
-
-
8-hydroxyquinoline
-
strong inhibition
acetone
-
inhibits competitively against 2-nitropropane, no inhibitory effect against O2
Butanal
-
competitive inhibitor with respect to ethylnitronate as substrate
cysteine
-
marked decrease in enzyme activity
EDTA
-
1 mM, relative activity remaining 95%
hexanal
-
competitive inhibitor with respect to ethylnitronate as substrate
iodoacetate
-
1 mM, complete inhibition
NADPH
-
competitive inhibitor. oxygenation is inhibited approximately 100% by 0.1 mM NADPH, respectively, although NAD+ and NADP+ are ineffective even at 1 mM. During the inhibition, NADH and NADPH are oxidized
nitrite
-
inhibits noncompetitively against 2-nitropropane, functioned as a noncompetitive inhibitor against oxygen in the presence of excess 2-nitropropane (50 mM)
Nitromethane
-
inhibits noncompetitively
pentanal
-
competitive inhibitor with respect to ethylnitronate as substrate
propanal
-
competitive inhibitor with respect to ethylnitronate as substrate
2-mercaptoethanol
-
-
2-mercaptoethanol
-
not inhibitory
2-mercaptoethanol
-
1 mM, relative activity remaining 2%
cytochrome c
-
competitive inhibitor
cytochrome c
-
O2 scavenger
cytochrome c
-
0.04 mM, relative activity remaining 34%
dithiothreitol
-
-
dithiothreitol
-
1 mM, complete inhibition
epinephrine
-
competitive inhibitor
GSH
-
marked decrease in enzyme activity
GSH
-
5 mM, relative activity remaining 28%
HgCl2
-
moderate and potent inhibitor
KBr
-
competitive inhibitor with respect to ethylnitronate as substrate
KCl
-
competitive inhibitor with respect to ethylnitronate as substrate
KF
-
competitive inhibitor with respect to ethylnitronate as substrate
KI
-
competitive inhibitor with respect to ethylnitronate as substrate
N-ethylmaleimide
-
-
NADH
-
competitive inhibitor. Oxygenation is inhibited approximately 86% by 0.1 mM NADH, although NAD+ and NADP+ are ineffective even at 1 mM. During the inhibition, NADH and NADPH are oxidized
NaNO2
-
competitive inhibitor with respect to ethylnitronate as substrate
NaNO2
-
competitive inhibitor with respect to ethylnitronate as substrate
NaNO3
-
competitive inhibitor with respect to ethylnitronate as substrate
NEM
-
-
Nitro blue tetrazolium
-
-
Nitro blue tetrazolium
-
2.5 mM, relative activity remaining 10%
p-chloromercuribenzoate
-
-
p-chloromercuribenzoate
-
-
PCMB
-
-
Superoxide dismutase
-
-
-
Superoxide dismutase
-
Cu and Zn-superoxide dismutase of bovine blood, Mn-superoxide dismutases of bacilli, Fe-superoxide dismutase of Serratia marcescens
-
Superoxide dismutase
-
not inhibitory
-
Superoxide dismutase
-
-
-
Superoxide dismutase
-
complete inhibition
-
Tiron
-
i.e. pyrocatechol-3,5-disulfonate disodium salt; i.e. pyrocatechol-3,5-disulfonate disodium salt, strong inhibition
Tiron
-
i.e. pyrocatechol-3,5-disulfonate disodium salt
additional information
-
EDTA does not inhibit the enzyme significantly. Iodoacetate is almost ineffective
-
additional information
-
inhibition by superoxide dismutase and various scavengers for superoxide; phenol, tryptophan, and tryptamine show no effect on the reaction
-
additional information
-
not affected by hydroxyl radical scavengers such as mannitol
-
additional information
superoxide dismutase and catalase have no effect on the enzymatic activity
-
additional information
-
superoxide dismutase and catalase have no effect on the enzymatic activity
-
additional information
-
8% (w/v) PEG 3350 shows no significant effect on the enzyme activity
-
additional information
-
no inhibition: tiron, superoxide dismutase, EDTA, cysteine, epinephrine, NADH, NADPH, and 2-mercaptoethanol
-
additional information
no inhibition by valeric acid and EDTA
-
additional information
-
no inhibition by valeric acid and EDTA
-
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29
1-nitroethane
pH and temperature not specified in the publication
-
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
0.45 - 91.4
1-Nitropropane
1.6 - 148.5
2-Nitropropane
0.59 - 4.2
3-Nitro-2-butanol
1.04 - 6.8
3-Nitro-2-pentanol
12
3-nitropropionic acid
-
at pH 7.4 and 30°C
10
butyl 1-nitronate
pH and temperature not specified in the publication
-
10
butyl-1-nitronate
in 50 mM Tris-HCl, pH 8 at 30°C
1.4
hexyl 1-nitronate
pH and temperature not specified in the publication
-
1.4
hexyl-1-nitronate
in 50 mM Tris-HCl, pH 8 at 30°C
0.06 - 0.15
propionate 3-nitronate
0.11 - 0.34
propionate-3-nitronate
5
propyl 1-nitronate
pH and temperature not specified in the publication
-
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
0.45
1-Nitropropane
at pH 6.5 and 28°C
1.3
1-Nitropropane
at pH 6.5 and 28°C
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
12.9
1-Nitropropane
at pH 6.5 and 28°C
13.6
1-Nitropropane
at pH 6.5 and 28°C
20
1-Nitropropane
-
neutral form of substrate
24
1-Nitropropane
in 50 mM Tris-HCl, pH 8 at 30°C
24
1-Nitropropane
pH and temperature not specified in the publication
25.6
1-Nitropropane
neutral form of substrate
25.6
1-Nitropropane
neutral form of the substrate
34.3
1-Nitropropane
at pH 6.5 and 28°C
91.4
1-Nitropropane
at pH 6.5 and 28°C
1.6
2-Nitropropane
at pH 6.5 and 28°C
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
2.8
2-Nitropropane
at pH 6.5 and 28°C
3.1
2-Nitropropane
-
anionic form of substrate
4.32
2-Nitropropane
at pH 6.5 and 28°C
5.6
2-Nitropropane
at pH 6.5 and 28°C
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
134.9
2-Nitropropane
at pH 6.5 and 28°C
148.5
2-Nitropropane
at pH 6.5 and 28°C
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
-
-
0.58
3-nitropropionate
-
pH 7.4, 30°C
0.58
3-nitropropionate
pH and temperature not specified in the publication
3.1
ethyl nitronate
in 50 mM Tris-HCl, pH 8 at 30°C
3.1
ethyl nitronate
pH and temperature not specified in the publication
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
3.4
nitroethane
at pH 6.5 and 28°C
6.8
nitroethane
neutral form of substrate
6.8
nitroethane
neutral form of the substrate
10.6
nitroethane
at pH 6.5 and 28°C
13
nitroethane
-
at pH 9.0 and 30°C
19
nitroethane
-
at pH 8.0 and 30°C
20.1
nitroethane
at pH 6.5 and 28°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
45.1
nitroethane
at pH 6.5 and 28°C
50.6
nitroethane
at pH 6.5 and 28°C
147.8
nitroethane
at pH 6.5 and 28°C
0.001
O2
-
Km less or equal 0.001 mM, with 3-nitropropionic acid as cosubstrate, at pH 7.4 and 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
0.009
O2
-
Km less or equal 0.009 mM, with propionate 3-nitronate as cosubstrate, at pH 7.4 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
0.06
propionate 3-nitronate
-
pH 5.5, 30°C
0.15
propionate 3-nitronate
-
at pH 7.4 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
0.34
propionate-3-nitronate
pH and temperature not specified in the publication
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
-
kinetic parameters of reductive half reaction
-
additional information
additional information
-
steady-state kinetic mechanism with ethylnitronate, overview
-
additional information
additional information
steady-state kinetic mechanism
-
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Kido, T.; Tanizawa, K.; Inagaki, K.; Yoshimura, T.; Ishida, M.; Hashizume, K.; Soda, K.
2-Nitropropane dioxygenase from Hansenula mrakii: re-characterization of the enzyme and oxidation of anionic nitroalkanes
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1984
Cyberlindnera mrakii, Cyberlindnera mrakii (Q12723)
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Kido, T.; Soda, K.; Suzuki, T.; Asada, K.
A new oxygenase, 2-nitropropane dioxygenase of Hansenula mrakii. Enzymologic and spectrophotometric properties
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1976
Cyberlindnera mrakii, Cyberlindnera mrakii IF0 0895
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Kido, T.; Soda, K.; Asada, K.
Properties of 2-nitropropane dioxygenase of Hansenula mrakii. Formation and participation of superoxide
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1978
Cyberlindnera mrakii, Cyberlindnera mrakii IF0 0895
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Kido, T.; Hashizume, K.; Soda, K.
Purification and properties of nitroalkane oxidase from Fusarium oxysporum
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Fusarium oxysporum
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Kido, T.; Tanizawa, K.; Ishida, M.; Inagaki, K.; Soda, K.
Characterization of primary nitroalkane oxidation by 2-nitropropane dioxygenase
Agric. Biol. Chem.
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1361-1362
1984
Cyberlindnera mrakii
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Kido, T.; Soda, K.
Oxidation of anionic nitroalkanes by flavoenzymes, and participation of superoxide anion in the catalysis
Arch. Biochem. Biophys.
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468-475
1984
Cyberlindnera mrakii
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Gorlatova, N.; Tchorzewski, M.; Kurihara, T.; Soda, K.; Esaki, N.
Purification, characterization, and mechanism of a flavin mononucleotide-dependent 2-nitropropane dioxygenase from Neurospora crassa
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1998
Neurospora crassa
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Gadda, G.; Fitzpatrick, P.F.
Substrate specificity of a nitroalkane-oxidizing enzyme
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Fusarium oxysporum
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Kido, T.; Yamamoto, T.; Soda, K.
Purification and properties of nitroalkane-oxidizing enzyme from Hansenula mrakii
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1976
Cyberlindnera mrakii
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Francis, K.; Russell, B.; Gadda, G.
Involvement of a flavosemiquinone in the enzymatic oxidation of nitroalkanes catalyzes by 2-nitropropane dioxygenase
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Neurospora crassa (Q01284), Neurospora crassa
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Francis, K.; Gadda, G.
Probing the chemical steps of nitroalkane oxidation catalyzed by 2-nitropropane dioxygenase with solvent viscosity, pH, and substrate kinetic isotope effects
Biochemistry
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13889-13898
2006
Neurospora crassa
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Ha, J.Y.; Min, J.Y.; Lee, S.K.; Kim, H.S.; Kim, d.o.J.; Kim, K.H.; Lee, H.H.; Kim, H.K.; Yoon, H.J.; Suh, S.W.
Crystal structure of 2-nitropropane dioxygenase complexed with FMN and substrate. Identification of the catalytic base
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Pseudomonas aeruginosa (Q9I4V0), Pseudomonas aeruginosa
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Mijatovic, S.; Gadda, G.
Oxidation of alkyl nitronates catalyzed by 2-nitropropane dioxygenase from Hansenula mrakii
Arch. Biochem. Biophys.
473
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2008
Cyberlindnera mrakii (Q12723), Cyberlindnera mrakii
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Francis, K.; Gadda, G.
The nonoxidative conversion of nitroethane to ethylnitronate in Neurospora crassa 2-nitropropane dioxygenase is catalyzed by Histidine 196
Biochemistry
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9136-9144
2008
Neurospora crassa
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Gadda, G.; Francis, K.
Nitronate monooxygenase, a model for anionic flavin semiquinone intermediates in oxidative catalysis
Arch. Biochem. Biophys.
493
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2009
Cyberlindnera saturnus, Neurospora crassa, Pseudomonas aeruginosa (Q9I4V0), Cyberlindnera saturnus mrakii
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Francis, K.; Gadda, G.
Inflated kinetic isotope effects in the branched mechanism of Neurospora crassa 2-nitropropane dioxygenase
Biochemistry
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2009
Neurospora crassa
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Francis, K.; Gadda, G.
Kinetic evidence for an anion binding pocket in the active site of nitronate monooxygenase
Bioorg. Chem.
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2009
Cyberlindnera mrakii, Neurospora crassa
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Balogh-Hergovich, E.; Kaizer, J.; Speier, G.
Copper mediated conversion of nitro compounds to aldehydes or ketones by dioxygen
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1996
Cyberlindnera mrakii
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Balogh-Hergovich, E.; Speier, G.; Huttner, G.; Zsolnai, L.
Copper-mediated oxygenation of nitronate to nitrite and acetone in a copper(I) nitronate complex
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Cyberlindnera mrakii
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Li, Y.; Gao, Z.; Hou, H.; Li, L.; Zhang, J.; Yang, H.; Dong, Y.; Tan, H.
Crystal structure and site-directed mutagenesis of a nitroalkane oxidase from Streptomyces ansochromogenes
Biochem. Biophys. Res. Commun.
405
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2011
Streptomyces ansochromogenes (Q9FDD4), Streptomyces ansochromogenes
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Francis, K.; Nishino, S.F.; Spain, J.C.; Gadda, G.
A novel activity for fungal nitronate monooxygenase: detoxification of the metabolic inhibitor propionate-3-nitronate
Arch. Biochem. Biophys.
521
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2012
Cyberlindnera saturnus, Neurospora crassa
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Smitherman, C.; Gadda, G.
Evidence for a transient peroxynitro acid in the reaction catalyzed by nitronate monooxygenase with propionate 3-nitronate
Biochemistry
52
2694-2704
2013
Cyberlindnera saturnus
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Klinkenberg, L.G.; Karakousis, P.C.
Rv1894c is a novel hypoxia-induced nitronate monooxygenase required for Mycobacterium tuberculosis virulence
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2013
Mycobacterium tuberculosis
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Vercammen, K.; Wei, Q.; Charlier, D.; Doetsch, A.; Hauessler, S.; Schulz, S.; Salvi, F.; Gadda, G.; Spain, J.; Rybtke, M.L.; Tolker-Nielsen, T.; Dingemans, J.; Ye, L.; Cornelis, P.
Pseudomonas aeruginosa LysR PA4203 regulator NmoR acts as a repressor of the PA4202 nmoA gene, encoding a nitronate monooxygenase
J. Bacteriol.
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2015
Pseudomonas aeruginosa (Q9HWH9), Pseudomonas aeruginosa
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Salvi, F.; Agniswamy, J.; Yuan, H.; Vercammen, K.; Pelicaen, R.; Cornelis, P.; Spain, J.C.; Weber, I.T.; Gadda, G.
The combined structural and kinetic characterization of a bacterial nitronate monooxygenase from Pseudomonas aeruginosa PAO1 establishes NMO class I and II
J. Biol. Chem.
289
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2014
Pseudomonas aeruginosa (Q9HWH9)
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Cervantes Quintero, K.Y.; Padilla Guerrero, I.E.; Torres Guzman, J.C.; Villa Martinez, B.G.; Valencia Felix, A.; Gonzalez Hernandez, G.A.
Members of the nitronate monooxygenase gene family from Metarhizium brunneum are induced during the process of infection to Plutella xylostella
Appl. Microbiol. Biotechnol.
104
2987-2997
2020
Metarhizium brunneum, Metarhizium brunneum (A0A6C0WVH0), Metarhizium brunneum (A0A6C0WVK2), Metarhizium brunneum (A0A6C0WW14), Metarhizium brunneum (A0A6C0WWH2), Metarhizium brunneum Ma10, Metarhizium brunneum Ma10 (A0A6C0WVH0), Metarhizium brunneum Ma10 (A0A6C0WVK2), Metarhizium brunneum Ma10 (A0A6C0WW14), Metarhizium brunneum Ma10 (A0A6C0WWH2)
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Torres-Guzman, J.; Padilla-Guerrero, I.; Cervantes-Quintero, K.; Martinez-Vazquez, A.; Ibarra-Guzman, M.; Gonzalez-Hernandez, G.
Peculiarities of nitronate monooxygenases and perspectives for in vivo and in vitro applications
Appl. Microbiol. Biotechnol.
105
8019-8032
2021
Neurospora crassa (Q01284), Neurospora crassa DSM 1257 (Q01284)
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Vodovoz, M.; Gadda, G.
Kinetic solvent viscosity effects reveal a protein isomerization in the reductive half-reaction of Neurospora crassa class II nitronate monooxygenase
Arch. Biochem. Biophys.
695
108625
2020
Neurospora crassa
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Su, D.; Kabir, M.P.; Orozco-Gonzalez, Y.; Gozem, S.; Gadda, G.
Fluorescence properties of flavin semiquinone radicals in nitronate monooxygenase
ChemBioChem
20
1646-1652
2019
Pseudomonas aeruginosa (Q9HWH9)
brenda
Agniswamy, J.; Reis, R.A.G.; Wang, Y.F.; Smitherman, C.; Su, D.; Weber, I.; Gadda, G.
Crystal structure of yeast nitronate monooxygenase from Cyberlindnera saturnus
Proteins
86
599-605
2018
Cyberlindnera saturnus
brenda