1.13.12.16: nitronate monooxygenase

This is an abbreviated version!
For detailed information about nitronate monooxygenase, go to the full flat file.

Word Map on EC 1.13.12.16

Reaction

ethylnitronate
+
O2
=
acetaldehyde
+
nitrite
+
other products

Synonyms

2-nitropropane dioxygenase, NAO, nitroalkane oxidase, nitroalkane-oxidizing enzyme, nitronate monooxygenase, nitropropane dioxygenase, NMO, NMO-Nc, NMO-Ws, nmoA, oxidase, nitroalkane, oxygenase, 2-nitropropane di-, P3N monooxygenase, Pa-NMO, PA4202, protein PA4202, Rv1894c, Sa-NAO

ECTree

     1 Oxidoreductases
         1.13 Acting on single donors with incorporation of molecular oxygen (oxygenases)
             1.13.12 With incorporation of one atom of oxygen (internal monooxygenases or internal mixed-function oxidases)
                1.13.12.16 nitronate monooxygenase

Substrates Products

Substrates Products on EC 1.13.12.16 - nitronate monooxygenase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-hydroxybutyl-2-nitronate + O2
3-hydroxy-butane-2-one + HNO2
show the reaction diagram
-
-
-
-
?
1-hydroxybutyl-2-nitronate + O2
? + HNO2
show the reaction diagram
-
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
show the reaction diagram
-
-
-
-
?
1-nitrobutane + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
1-nitrobutane + O2
butyraldehyde + HNO2
show the reaction diagram
1-nitrobutane + O2
butyraldehyde + nitrite
show the reaction diagram
-
-
-
?
1-nitrohexane + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
1-nitrohexane + O2
hexanaldehyde + HNO2
show the reaction diagram
1-nitrohexane + O2
hexanaldehyde + nitrite
show the reaction diagram
-
-
-
?
1-nitropentane + O2
? + HNO2
show the reaction diagram
1-nitropentane + O2
pentanaldehyde + HNO2
show the reaction diagram
1-nitropentane + O2
pentanaldehyde + nitrite
show the reaction diagram
-
-
-
?
1-nitropropane + O2
1,1-dinitropropane + HNO2
show the reaction diagram
-
-
-
-
?
1-nitropropane + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
1-nitropropane + O2
propionaldehyde + HNO2
show the reaction diagram
1-nitropropane + O2
propionaldehyde + nitrite
show the reaction diagram
-
-
-
?
1-nitropropane + O2 + H2O
propionaldehyde + HNO2 + H2O2
show the reaction diagram
-
-
-
-
?
2 Cu((CH3)2CNO2)(PPh3)2 + O2
2 Cu(O2N)(PPh3)2 + 2 propan-2-one
show the reaction diagram
-
using a copper(I) aci-2-nitropropanate complex
-
-
?
2-hydroxybutyl-3-nitronate + O2
? + HNO2
show the reaction diagram
-
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
show the reaction diagram
-
-
-
-
?
2-hydroxypentyl-3-nitronate + O2
? + HNO2
show the reaction diagram
-
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
show the reaction diagram
2-nitro-1-propanol + O2
1-hydroxy-propane-2-one + HNO2
show the reaction diagram
2-nitro-1-propanol + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
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
show the reaction diagram
-
with N,N-dimethylformamid (conversion: 30%) as solvent
-
-
?
2-nitroethanol + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
2-nitroethanol + O2
glycoaldehyde + HNO2
show the reaction diagram
-
13% of the activity with 2-nitropropane
-
-
?
2-nitroethanol + O2 + H2O
? + HNO2 + H2O2
show the reaction diagram
-
8.4% relative activity (1-nitropropane: 100%)
-
-
?
2-nitropropane + O2
?
show the reaction diagram
-
-
-
?
2-nitropropane + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
2-nitropropane + O2
acetone + HNO2
show the reaction diagram
2-nitropropane + O2
acetone + nitrite
show the reaction diagram
-
-
-
?
2-nitropropane + O2 + H2O
acetone + HNO2 + H2O2
show the reaction diagram
-
96.9% relative activity (1-nitropropane: 100%)
-
-
?
3 propionate-3-nitronate + O2
3 malonic semialdehyde + nitrite + 2 nitrate + H2O2
show the reaction diagram
3-nitro-1-butanol + O2 + H2O
? + HNO2 + H2O2
show the reaction diagram
-
15.7% relative activity (1-nitropropane: 100%)
-
-
?
3-nitro-2-butanol + O2
3-hydroxy-butane-2-one + HNO2
show the reaction diagram
3-nitro-2-butanol + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
3-nitro-2-butanol + O2 + H2O
? + HNO2 + H2O2
show the reaction diagram
-
6.5% relative activity (1-nitropropane: 100%)
-
-
?
3-nitro-2-pentanol + O2
2-hydroxy-pentane-3-one + HNO2
show the reaction diagram
3-nitro-2-pentanol + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
3-nitro-2-pentanol + O2 + H2O
2-hydroxy-pentane-3-one + HNO2 + H2O2
show the reaction diagram
-
116% relative activity (1-nitropropane: 100%)
-
-
?
3-nitropropionate + O2
?
show the reaction diagram
-
-
-
-
?
3-nitropropionate + O2 + H2O
? + HNO2 + H2O2
show the reaction diagram
-
0.5% relative activity (1-nitropropane: 100%)
-
-
?
3-nitropropionic acid + O2
?
show the reaction diagram
butyl-1-nitronate + O2
?
show the reaction diagram
-
-
-
?
butyl-1-nitronate + O2
? + nitrite
show the reaction diagram
butyl-1-nitronate + O2
NO2- + butanal
show the reaction diagram
-
-
-
?
cyclohexyl nitronate + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
ethyl nitronate + O2
? + nitrite
show the reaction diagram
ethyl nitronate + O2
acetaldehyde + HNO2
show the reaction diagram
-
-
-
-
?
ethylnitronate + Cu(0) + N,N,N',N'-tetramethylethylenediamine + O2
acetone + (NO2)CuN,N,N',N'-tetramethylethylenediamine
show the reaction diagram
-
with N,N-dimethylformamid (conversion: 60%) and pyridine (conversion: 90%) as solvent
-
-
?
ethylnitronate + O2
acetaldehyde + HNO2
show the reaction diagram
ethylnitronate + O2
acetaldehyde + nitrite + other products
show the reaction diagram
-
-
-
?
ethylnitronate + O2
NO2- + acetaldehyde
show the reaction diagram
-
-
-
?
ethylnitronate + O2 + FMNH2
acetaldehyde + nitrite + FMN + H2O
show the reaction diagram
hexyl-1-nitronate + O2
? + nitrite
show the reaction diagram
hexyl-1-nitronate + O2
NO2- + hexanal
show the reaction diagram
-
-
-
?
nitrocyclohexane + O2
? + HNO2
show the reaction diagram
nitrocyclohexane + O2
cyclohexanone + HNO2
show the reaction diagram
nitrocyclohexane + O2 + H2O
cyclohexanone + HNO2 + H2O2
show the reaction diagram
-
99.8% relative activity (1-nitropropane: 100%)
-
-
?
nitrocyclopentane + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
nitroethane + O2
? + nitrite
show the reaction diagram
-
-
-
-
?
nitroethane + O2
acetaldehyde + HNO2
show the reaction diagram
nitroethane + O2
acetaldehyde + HNO2 + 1,1-dinitroethane
show the reaction diagram
-
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
show the reaction diagram
nitroethane + O2
ethanal + nitrite
show the reaction diagram
nitroethane + O2
ethylnitronate
show the reaction diagram
-
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
show the reaction diagram
-
51.8% relative activity (1-nitropropane: 100%)
-
-
?
nitroethane + O2 + H2O
ethanal + nitrite + H2O2
show the reaction diagram
nitromethane + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
nitromethane + O2
formaldehyde + HNO2
show the reaction diagram
nitromethane + O2 + H2O
? + HNO2 + H2O2
show the reaction diagram
-
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
show the reaction diagram
-
with N,N-dimethylformamid (conversion: 28%) and pyridine (conversion: 21%) as solvent
-
-
?
pentyl-1-nitronate + O2
?
show the reaction diagram
-
-
-
?
pentyl-1-nitronate + O2
? + HNO2
show the reaction diagram
-
-
-
-
?
pentyl-1-nitronate + O2
? + nitrite
show the reaction diagram
pentyl-1-nitronate + O2
NO2- + pentanal
show the reaction diagram
-
-
-
?
propionate 3-nitronate + O2
?
show the reaction diagram
-
-
-
-
?
propionate-3-nitronate + O2
?
show the reaction diagram
propyl-1-nitronate + O2
?
show the reaction diagram
propyl-1-nitronate + O2
? + nitrite
show the reaction diagram
propyl-1-nitronate + O2
NO2- + propionaldehyde
show the reaction diagram
-
-
-
?
propyl-1-nitronate + O2
propionaldehyde + HNO2
show the reaction diagram
-
-
-
-
?
propyl-1-nitronate + O2 + FMNH2
? + nitrite + FMN + H2O
show the reaction diagram
-
-
-
-
?
propyl-2-nitronate + Cu(0) + 1,10-phenanthroline + O2
propan-2-one + ?
show the reaction diagram
-
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 + ?
show the reaction diagram
-
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
show the reaction diagram
-
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 + ?
show the reaction diagram
-
without ligand and without solvent (conversion: 12%)
-
-
?
propyl-2-nitronate + O2
?
show the reaction diagram
-
-
-
?
propyl-2-nitronate + O2
? + nitrite
show the reaction diagram
propyl-2-nitronate + O2
acetone + HNO2
show the reaction diagram
propyl-2-nitronate + O2
NO2- + acetone
show the reaction diagram
-
-
-
?
propyl-2-nitronate + O2 + FMNH2
? + nitrite + FMN + H2O
show the reaction diagram
propylnitronate + O2
? + HNO2
show the reaction diagram
-
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
show the reaction diagram
-
with N,N-dimethylformamid (conversion: 66%) and pyridine (conversion: 67%) as solvent
-
-
?
additional information
?
-