Information on EC 1.2.99.7 - aldehyde dehydrogenase (FAD-independent)

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.2.99.7
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RECOMMENDED NAME
GeneOntology No.
aldehyde dehydrogenase (FAD-independent)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an aldehyde + H2O + acceptor = a carboxylate + reduced acceptor
show the reaction diagram
Belongs to the xanthine oxidase family of enzymes. The enzyme from Desulfovibrio sp. contains a molybdenum-molybdopterin-cytosine dinucleotide (MCD) complex and two types of [2Fe-2S] cluster per monomer, but does not contain FAD
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
aldehyde:acceptor oxidoreductase (FAD-independent)
Belongs to the xanthine oxidase family of enzymes. The enzyme from Desulfovibrio sp. contains a molybdenum-molybdopterin-cytosine dinucleotide (MCD) complex and two types of [2Fe-2S] cluster per monomer, but does not contain FAD.
CAS REGISTRY NUMBER
COMMENTARY hide
9029-07-6
cf. EC 1.2.3.1
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
NCIMB 1349; NCIMB 13491
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Manually annotated by BRENDA team
KY 469
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Manually annotated by BRENDA team
KY 469
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2,3-dihydroxybenzaldehyde + H2O + 2,6-dichlorophenol-indophenol
2,3-dihydroxybenzoate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
2,5-dihydroxybenzaldehyde + H2O + 2,6-dichlorophenol-indophenol
2,5-dihydroxybenzoate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
2-phenylacetaldehyde + H2O + 2,6-dichlorophenol-indophenol
2-phenylacetate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
3-hydroxybenzaldehyde + H2O + 2,6-dichlorophenol-indophenol
3-hydroxybenzoate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
3-phenylpropanal + H2O + 2,6-dichlorophenol-indophenol
3-phenylpropanoate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
3-pyridinecarboxaldehyde + H2O + 2,6-dichlorophenol-indophenol
3-pyridinecarboxylate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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159% of activity with acetaldehyde
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?
acetaldehyde + H2O + 2,6-dichlorophenol-indophenol
acetate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
acetaldehyde + H2O + 2,6-dichlorophenolindophenol
acetate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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?
acetaldehyde + H2O + acceptor
acetate + reduced acceptor
show the reaction diagram
acetaldehyde + H2O + benzylviologen
acetate + reduced benzylviologen
show the reaction diagram
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natural electron aceptor not yet known, the artificial electron acceptors benzylviologen, methylviologen, 2,3-bis-(2-methoxy-4-nitro-5-sulfophenyl) and 2,6-dichlorphenol-indophenol have relative activities of 100%, 19%, 5%, and 1.3%, respectively
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?
acetaldehyde + H2O + electron acceptor
acetate + reduced acceptor
show the reaction diagram
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?
acetaldehyde + H2O + electron acceptor
acetate + reduced electron acceptor
show the reaction diagram
aldehyde + H2O + acceptor
carboxylate + reduced acceptor
show the reaction diagram
benzaldehyde + 2 ferricyanide + H2O
benzoate + 2 ferrocyanide + 2 H+
show the reaction diagram
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156% of activity with 2,6-dichlorophenol-indophenol
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?
benzaldehyde + H2O + 2,6-dichlorophenol-indophenol
benzoate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
benzaldehyde + H2O + 2,6-dichlorophenolindophenol
benzoate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
benzaldehyde + H2O + 2,6-dichlorophenolindophenol
benzoate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
benzaldehyde + H2O + benzylviologen
benzoate + reduced benzylviologen
show the reaction diagram
benzaldehyde + H2O + cytochrome c
benzoate + reduced cytochrome c
show the reaction diagram
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from horse heart, 25% of activity with 2,6-dichlorophenol-indophenol
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?
benzaldehyde + H2O + cytochrome c3
benzoate + reduced cytochrome c3
show the reaction diagram
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from, Desulfovibrio gigas, 20% of activity with 2,6-dichlorophenol-indophenol
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?
benzaldehyde + H2O + electron acceptor
benzoate + reduced electron acceptor
show the reaction diagram
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?
benzaldehyde + H2O + methylene blue
benzoate + reduced methylene blue
show the reaction diagram
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156% of activity with 2,6-dichlorophenol-indophenol
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?
benzaldehyde + H2O + oxidized 2,6-dichlorophenolindophenol
benzoate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
butyraldehyde + H2O + benzylviologen
butanoate + reduced benzylviologen
show the reaction diagram
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93% of activity with acetaldehyde
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?
cinnamaldehyde + H2O + 2,6-dichlorophenol-indophenol
cinnamate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
formaldehyde + H2O + benzylviologen
formate + reduced benzylviologen
show the reaction diagram
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16% of activity with acetaldehyde
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?
furfural + H2O + benzylviologen
furfurate + reduced benzylviologen
show the reaction diagram
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77% of activity with acetaldehyde
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?
furfuraldehyde + H2O + 2,6-dichlorophenol-indophenol
furfurate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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27% of activity with acetaldehyde
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?
glutaraldehyde + H2O + benzylviologen
glutarate + reduced benzylviologen
show the reaction diagram
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20% of activity with acetaldehyde
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?
glycoaldehyde + H2O + benzylviologen
glycolate + reduced benzylviologen
show the reaction diagram
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23% of activity with acetaldehyde
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?
hexanal + H2O + benzylviologen
hexanoate + reduced benzylviologen
show the reaction diagram
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6% of activity with acetaldehyde
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?
octanal + H2O + benzylviologen
octanoate + reduced benzylviologen
show the reaction diagram
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93% of activity with acetaldehyde
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?
p-anisaldehyde + H2O + benzylviologen
p-anisidic acid + reduced benzylviologen
show the reaction diagram
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5% of activity with acetaldehyde
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?
pentanal + H2O + benzylviologen
pentanoate + reduced benzylviologen
show the reaction diagram
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9% of activity with acetaldehyde
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?
phenylacetaldehyde + H2O + benzylviologen
phenylacetate + reduced benzylviologen
show the reaction diagram
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31% of activity with acetaldehyde
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?
propionaldehyde + H2O + 2,6-dichlorophenol-indophenol
propionate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
propionaldehyde + H2O + 2,6-dichlorophenolindophenol
propionate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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?
propionaldehyde + H2O + benzylviologen
propionate + reduced benzylviologen
show the reaction diagram
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117% of activity with acetaldehyde
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?
salicylaldehyde + H2O + 2,6-dichlorophenol-indophenol
salicylate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
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?
salicylaldehyde + H2O + 2,6-dichlorophenolindophenol
salicylate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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?
salicylaldehyde + H2O + benzylviologen
salicylate + reduced benzylviologen
show the reaction diagram
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14% of activity with acetaldehyde
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
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the enzyme also catalyzes the nitrite reduction with nitric oxide formation in an enzyme-, aldehyde- and nitrite-concentration- dependent manner. The enzyme catalyzes the nitrite reduction to nitric oxide in the presence of an electron donor to the enzyme, substrate (aldehyde) or not (dithionite)
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
[2Fe-2S]-center
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the enzyme contains two [2Fe2S] centers
additional information
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the enzyme contains no FAD
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
K+
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10 mM, 50% activation
Molybdenum
Tungsten
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0.68 tungsten per subunit
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-phenylacetaldehyde
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substrate inhibition at high concentrations
3-phenylpropanal
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substrate inhibition at high concentrations, suicide substrate
arsenite
benzaldehyde
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substrate inhibition at high concentrations
cinnamaldehyde
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substrate inhibition at high concentrations
cyanide
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competitive reversible inhibitor, 30.9% inhibition at 50 mM
ethylene glycol
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mixed-type reversible inhibitor, 21.9% inhibition at 1 mM
glycerol
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competitive reversible inhibitor, 52% inhibition at 1 mM
iodoacetate
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5 mM, complete inhibition
KCN
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5 mM, 64% inhibition
methanol
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1 M, 62% inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.044
2,3-Dihydroxybenzaldehyde
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pH 7.6, 35C
3.457
2,5-dihydroxybenzaldehyde
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pH 7.6, 35C
0.27
2-phenylacetaldehyde
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pH 7.6, 35C
0.117
3-Hydroxybenzaldehyde
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pH 7.6, 35C
0.029
3-phenylpropanal
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pH 7.6, 35C
0.013 - 12.5
acetaldehyde
0.0067 - 20
benzaldehyde
0.55
benzylviologen
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30C, pH 7.5
0.008
cinnamaldehyde
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pH 7.6, 35C
30.8
furfural
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30C, pH 7.5
0.015 - 10.8
propionaldehyde
0.00025 - 0.0016
Salicylaldehyde
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.87
2,3-Dihydroxybenzaldehyde
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pH 7.6, 35C
3.3
2,5-dihydroxybenzaldehyde
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pH 7.6, 35C
4.4
2-phenylacetaldehyde
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pH 7.6, 35C
3.6
3-Hydroxybenzaldehyde
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pH 7.6, 35C
2.1
3-phenylpropanal
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pH 7.6, 35C
0.12 - 1.14
acetaldehyde
0.96 - 5.7
benzaldehyde
0.58
cinnamaldehyde
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pH 7.6, 35C
0.007 - 0.44
propionaldehyde
0.15 - 0.44
Salicylaldehyde
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
20
2,3-Dihydroxybenzaldehyde
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pH 7.6, 35C
1
2,5-dihydroxybenzaldehyde
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pH 7.6, 35C
16
2-phenylacetaldehyde
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pH 7.6, 35C
31
3-Hydroxybenzaldehyde
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pH 7.6, 35C
72
3-phenylpropanal
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pH 7.6, 35C
228
benzaldehyde
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pH 7.6, 35C
73
cinnamaldehyde
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pH 7.6, 35C
275
Salicylaldehyde
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pH 7.6, 35C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4
2-phenylacetaldehyde
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Kis value, pH 7.6, 35C
0.6
3-phenylpropanal
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Kis value, pH 7.6, 35C
0.8
benzaldehyde
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Kis value, pH 7.6, 35C
0.6
cinnamaldehyde
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Kis value, pH 7.6, 35C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8
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broad optimum
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
62000
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2 * 62000, SDS-PAGE
96000
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2 * 96000, SDS-PAGE
100000
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2 * 100000, SDS-PAGE
120000
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gelfiltration, Sephacryl S-300
126000
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gel filtration, Superose 12 HR
200000
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gel filtration
206000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure at 2.25 A resolution
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kinetic and X-ray crystallographic study, structures of inactive and activated enzyme. Activation/inactivation is governed by the oxidation state of the dithiolene moiety of the pyranopterin cofactor. Incubation with dithionite plus sulfide in the presence of dioxygen produces hydrogen peroxide not associated with the enzyme activation. The peroxide molecule coordinates to molybdenum in a ny2 fashion inhibiting the enzyme activity
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sitting drop vapor diffusion method, using 30% (v/v) 2-propanol, 0.2 M magnesium chloride, and 0.2 M HEPES buffer (pH 7.6)
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vapour diffusion on sitting drops using a mixture of purified protein in 10 mM Tris-HCl, pH 7.5, and a crystallization solution of 30% isopropanol as precipitant and 200 mM MgCl2 as additive in 200 mM HEPES, pH 7.6, growth of crystals at 4C takes approx. 3 weeks, crystals diffract to 1.28 A
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vapour-diffusion using sitting drops and a reservoir containing 100 mM Hepes, pH 7.5, 200 mM MgCl2 and 30% isopropanol, droplets are prepared by mixing 0.004 ml of a 13 mg/ml protein solution in 10 mM Tris, pH 7.6 with 0.002 ml reservoir solution, single crystals are obtained within 3-6 weeks at 4C, crystals diffract to 3.0 A
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
exposure to air leads to inactivation
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11936
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-30C, phosphate buffer, no loss of activity after thawing
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
aerobic purification
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DEAE-52, DEAE-Biogel, hydroxylapatite, HPLC
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DEAE-cellulose, Source-15, Superdex 200
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Q-Sepharose, Butyl-Sepharose, DEAE-memsep 1010
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Show AA Sequence (207 entries)
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