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ethylnitronate + O2 = acetaldehyde + nitrite + other products
ethylnitronate + O2 = acetaldehyde + nitrite + other products
superoxide as reactive intermediate
-
ethylnitronate + O2 = acetaldehyde + nitrite + other products
ordered bi bi mechanism in which 2-nitropropane first combines with the enzyme and the enzyme 2-nitropropane complex reacts with oxygen to form a ternary complex
-
ethylnitronate + O2 = acetaldehyde + nitrite + other products
catalytic and kinetic reaction mechanism, comparison to the nitroalkane oxigenase, EC 1.7.3.1, and other flavin-dependent enzymes, ionization of nitroethane and ethylnitronate in aqueous solution, overview. Enzymatic turnover begins with the rapid equilibrium association of ethylnitronate and the enzyme. In the oxidative pathway, the transfer of a single electron oxidizes the organic substrate and reduces the enzyme-bound flavin to an anionic semiquinone species, the electron transfer occurs while the substrate radical is still bound in the active site of the enzyme. After formation of the flavosemiquinone species in the active site of NMO, the subsequent oxidation of the one electron reduced flavin occurs when molecular oxygen reacts with the anionic flavosemiquinone to yield an enzyme-associated superoxide species, with second-order rate constants
-
ethylnitronate + O2 = acetaldehyde + nitrite + other products
catalytic and kinetic reaction mechanism, comparison to the nitroalkane oxygenase, EC 1.7.3.1, and other flavin-dependent enzymes, ionization of nitroethane and ethylnitronate in aqueous solution, overview
-
ethylnitronate + O2 = acetaldehyde + nitrite + other products
catalytic and kinetic reaction mechanism, comparison to the nitroalkane oxygenase, EC 1.7.3.1, and other flavin-dependent enzymes, ionization of nitroethane and ethylnitronate in aqueous solution, overview
ethylnitronate + O2 = acetaldehyde + nitrite + other products
catalyze the oxidation of propionate-3-nitronate or other nitronate analogues through a radical mechanism involving a catalytic flavosemiquinone without formation of a canonical C4a-(hydro)peroxyflavin
ethylnitronate + O2 = acetaldehyde + nitrite + other products
superoxide as reactive intermediate
-
-
ethylnitronate + O2 = acetaldehyde + nitrite + other products
ordered bi bi mechanism in which 2-nitropropane first combines with the enzyme and the enzyme 2-nitropropane complex reacts with oxygen to form a ternary complex
-
-
ethylnitronate + O2 = acetaldehyde + nitrite + other products
catalytic and kinetic reaction mechanism, comparison to the nitroalkane oxygenase, EC 1.7.3.1, and other flavin-dependent enzymes, ionization of nitroethane and ethylnitronate in aqueous solution, overview
-
-
ethylnitronate + O2 = acetaldehyde + nitrite + other products
-
-
-
-
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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
-
-
1.13.12.16 nitronate monooxygenase
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