Information on EC 1.2.99.6 - carboxylate reductase

Word Map on EC 1.2.99.6
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Bacteria, Archaea

EC NUMBER
COMMENTARY hide
1.2.99.6
-
RECOMMENDED NAME
GeneOntology No.
carboxylate reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
An aldehyde + acceptor + H2O = a carboxylate + reduced acceptor
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Pyruvate metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
aldehyde:acceptor oxidoreductase
A tungsten protein. Methyl viologen can act as acceptor. In the reverse direction, non-activated acids are reduced by reduced viologens to aldehydes, but not to the corresponding alcohols.
CAS REGISTRY NUMBER
COMMENTARY hide
125008-36-8
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain NCIMB 9332
-
-
Manually annotated by BRENDA team
no activity in Butyribacterium methylotrophicum
-
-
-
Manually annotated by BRENDA team
no activity in Clostridium aceticum
-
-
-
Manually annotated by BRENDA team
no activity in Eubacterium limosum
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain ES-1
-
-
Manually annotated by BRENDA team
strain ES-1
-
-
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
3,4-Dimethoxy-5-hydroxy-benzaldehyde + carbamoyl methyl viologen
3,4-Dimethoxy-5-hydroxy-benzoate + reduced carbamoyl methyl viologen
show the reaction diagram
-
-
-
-
-
3,5-Dimethoxy-4-hydroxy-benzaldehyde + carbamoyl methyl viologen
3,5-Dimethoxy-4-hydroxy-benzoate + reduced carbamoyl methyl viologen
show the reaction diagram
-
-
-
-
-
3-Chlorobenzoate + reduced carbamoyl methyl viologen
3-Chlorobenzaldehyde + carbamoyl methyl viologen
show the reaction diagram
3-Fluorobenzoate + reduced carbamoyl methyl viologen
3-Fluorobenzaldehyde + carbamoyl methyl viologen
show the reaction diagram
3-Hydroxybenzoate + reduced carbamoyl methyl viologen
3-Hydroxybenzaldehyde + carbamoyl methyl viologen
show the reaction diagram
3-Methoxybenzoate + reduced carbamoyl methyl viologen
3-Methoxybenzaldhyde + carbamoyl methyl viologen
show the reaction diagram
3-Methylbenzoate + reduced carbamoyl methyl viologen
3-Methylbenzaldehyde + carbamoyl methyl viologen
show the reaction diagram
4-(Hydroxymethyl)benzoate + reduced carbamoyl methyl viologen
4-(Hydroxymethyl)benzaldehyde + carbamoyl methyl viologen
show the reaction diagram
-
-
-
-
-
4-Chlorobenzoate + reduced carbamoyl methyl viologen
4-Chlorobenzaldehyde + carbamoyl methyl viologen
show the reaction diagram
4-Fluorobenzoate + reduced carbamoyl methyl viologen
4-Fluorobenzaldehyde + carbamoyl methyl viologen
show the reaction diagram
4-Hydroxy-3-methoxy-benzaldehyde + carbamoyl methyl viologen
4-Hydroxy-3-methoxy-benzoate + reduced carbamoyl methyl viologen
show the reaction diagram
-
-
-
-
-
4-Hydroxybenzaldehyde + carbamoyl methyl viologen
4-Hydroxybenzoate + reduced carbamoyl methyl viologen
show the reaction diagram
-
r
-
-
4-Hydroxybenzoate + reduced carbamoyl methyl viologen
4-Hydroxybenzaldehyde + carbamoyl methyl viologen
show the reaction diagram
-
-
-
-
-
4-Methoxybenzaldehyde + benzyl viologen
4-Methoxybenzoate + reduced carbamoyl methyl viologen
show the reaction diagram
4-Methoxybenzoate + reduced carbamoyl methyl viologen
4-Methoxybenzaldehyde + carbamoyl methyl viologen
show the reaction diagram
-
-
-
-
-
4-Methylbenzoate + reduced carbamoyl methyl viologen
4-Methylbenzaldehyde + carbamoyl methyl viologen
show the reaction diagram
5-Phenyl-2,4-pentadienate + reduced carbamoyl methyl viologen
? + carbamoyl methyl viologen
show the reaction diagram
-
-
-
-
-
Acetaldehyde + 2,6-dichlorophenol-indophenol
acetate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
Acetaldehyde + 3-(4',5'-dimethylthiazol-2-yl)-2,4-diphenyltetrazolium bromide
acetate + reduced 3-(4',5'-dimethylthiazol-2-yl)-2,4-diphenyltetrazolium bromide
show the reaction diagram
Acetaldehyde + benzyl viologen
acetate + reduced benzyl viologen
show the reaction diagram
acetaldehyde + benzyl viologen
acetic acid + reduced benzyl viologen
show the reaction diagram
-
-
-
-
?
Acetaldehyde + carbamoyl methyl viologen
acetate + reduced carbamoyl methyl viologen
show the reaction diagram
-
r
-
-
Acetaldehyde + methyl viologen
acetate + reduced methyl viologen
show the reaction diagram
benzaldehyde + 2,6-dichlorophenol indophenol
benzoate + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
-
-
-
-
?
Benzaldehyde + benzyl viologen
Benzoate + reduced benzyl viologen
show the reaction diagram
benzaldehyde + benzyl viologen
benzoic acid + reduced benzyl viologen
show the reaction diagram
-
96% of activity compared to acetaldehyde
-
-
?
Benzaldehyde + carbamoyl methyl viologen
Benzoate + reduced carbamoyl methyl viologen
show the reaction diagram
Butanal + methyl viologen
Butanoate + reduced methyl viologen
show the reaction diagram
-
-
-
-
-
Butanal + NH2CO-methyl viologen
Butanoate + reduced NH2CO-methyl viologen
show the reaction diagram
Butyraldehyde + benzyl viologen
Butanoate + reduced benzyl viologen
show the reaction diagram
Cinnamaldehyde + carbamoyl methyl viologen
Cinnamate + reduced carbamoyl methyl viologen
show the reaction diagram
-
r
-
-
crotonaldehyde + benzyl viologen
crotonic acid + reduced benzyl viologen
show the reaction diagram
-
47% of activity compared to acetaldehyde
-
-
?
Crotonaldehyde + benzyl viologen
E-2-Butenoate + reduced benzyl viologen
show the reaction diagram
-
at less than 1% of the activity with benzyl viologen
-
-
-
Crotonaldehyde + ES-1 ferredoxin
Crotonate + reduced ES-1 ferredoxin
show the reaction diagram
-
-
-
-
-
Crotonaldehyde + methyl viologen
Crotonate + reduced methyl viologen
show the reaction diagram
decylaldehyde + 2,6-dichlorophenol indophenol
decanoate + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
-
-
-
-
?
DL-glyceraldehyde + benzyl viologen
alpha,beta-dihydroxypropionic acid + reduced benzyl viologen
show the reaction diagram
-
9% of activity compared to acetaldehyde
-
-
?
formaldehyde + benzyl viologen
formic acid + reduced benzyl viologen
show the reaction diagram
-
2% of activity compared to acetaldehyde
-
-
?
Furfural + benzyl viologen
2-Furancarboxylic acid + reduced benzyl viologen
show the reaction diagram
-
at 77% of the activity relative to acetaldehyde
-
-
-
Glutaraldehyde + benzyl viologen
Glutarate + reduced benzyl viologen
show the reaction diagram
-
at 16% of the activity relative to acetaldehyde
-
-
-
glutaraldehyde + benzyl viologen
glutaric acid + reduced benzyl viologen
show the reaction diagram
-
19% of activity compared to acetaldehyde
-
-
?
Glyceraldehyde + benzyl viologen
Glycerate + reduced benzyl viologen
show the reaction diagram
-
-
-
-
-
Glyceraldehyde + methyl viologen
Glycerate + reduced methyl viologen
show the reaction diagram
-
-
-
-
-
Glycolaldehyde + benzyl viologen
Glycolate + reduced benzyl viologen
show the reaction diagram
-
at 23% of the activity relative to acetaldehyde
-
-
-
glyoxylate + benzyl viologen
oxalic acid + reduced benzyl viologen
show the reaction diagram
-
6% of activity compared to acetaldehyde
-
-
?
Hexanal + benzyl viologen
Hexanoate + reduced benzyl viologen
show the reaction diagram
-
at 6% of the activity relative to acetaldehyde
-
-
-
Indoleacetaldehyde + benzyl viologen
Indoleacetate + reduced benzyl viologen
show the reaction diagram
isovaleraldehyde + benzyl viologen
isopentanoic acid + reduced benzyl viologen
show the reaction diagram
-
66% of activity compared to acetaldehyde
-
-
?
Isovaleraldehyde + benzyl viologen
Isovalerate + reduced benzyl viologen
show the reaction diagram
Methanal + benzyl viologen
Formate + reduced benzyl viologen
show the reaction diagram
Methanal + carbamoyl methyl viologen
Formate + reduced methyl viologen
show the reaction diagram
-
-
-
-
-
Methanal + methyl viologen
Formate + reduced carbamoyl methyl viologen
show the reaction diagram
-
-
-
-
-
octanal + 2,6-dichlorophenol indophenol
octanoate + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
-
-
-
-
?
Pentanal + benzyl viologen
Pentanoate + reduced benzyl viologen
show the reaction diagram
-
at 9% of the activity relative to acetaldehyde
-
-
-
Phenylacetaldehyde + benzyl viologen
Phenylacetate + reduced benzyl viologen
show the reaction diagram
phenylacetaldehyde + benzyl viologen
phenylacetic acid + reduced benzyl viologen
show the reaction diagram
-
20% of activity compared to acetaldehyde
-
-
?
Propanal + benzyl viologen
Propanoate + reduced benzyl viologen
show the reaction diagram
Propanal + methyl viologen
Propanoate + reduced methyl viologen
show the reaction diagram
Propanal + NH2CO-methyl viologen
Propanoate + reduced carbamoyl methyl viologen
show the reaction diagram
Propanal + reduced 1,1',2,2'-tetramethylviologen
Propanoate + 1,1',2,2'-tetramethylviologen
show the reaction diagram
-
-
-
-
-
propionaldehyde + benzyl viologen
propionic acid + reduced benzyl viologen
show the reaction diagram
-
119% of activity compared to acetaldehyde
-
-
?
Pyridine 4-carboxylate + reduced carbamoyl methyl viologen
Pyridine 4-carboxaldehyde + carbamoyl methyl viologen
show the reaction diagram
-
-
-
-
-
Salicylaldehyde + benzyl viologen
Salicylate + reduced benzyl viologen
show the reaction diagram
salicylaldehyde + benzyl viologen
salicylic acid + reduced benzyl viologen
show the reaction diagram
-
4% of activity compared to acetaldehyde
-
-
?
terephthalaldehyde + carbamoyl methyl viologen
terephthalate + reduced carbamoyl methyl viologen
show the reaction diagram
-
r
-
-
additional information
?
-
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
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
-
the heptameric enzyme form contains 1.7 mol of FAD per mol of enzyme, seems to be a component of the gamma-subunit
molybdopterin
pterin
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
the enzyme contains 0.7 gatom of Ca per mol of enzyme
K+
-
stimulates, optimal concentration: 10 mM
Mg2+
-
enzyme contains 1.1 gatom of Mg per mol of enzyme
Tungsten
Zn2+
-
the enzyme contains 0.2 gatom of Zn per mol of enzyme
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,2'-bipyridyl
-
-
2-Hydroxypyridine-5-carboxylate
-
-
acetaldehyde
-
5 mM, 50% inhibition
AsO2-
Chloralhydrate
-
tungsten-containing enzyme
crotonaldehyde
-
above 0.2 mM
iodoacetate
Isovaleraldehyde
-
4 mM, 50% inhibition
K3Fe(CN)6
-
tungsten-containing enzyme and molybdenum-containing enzyme
methanol
-
-
phenylacetaldehyde
-
7 mM, 50% inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
10
3,5-dimethoxy-4-hydroxybenzaldehyde
-
with carbamoyl methyl viologen as cosubstrate
2.4 - 3.8
3-chlorobenzoate
3.5
3-Fluorobenzoate
-
with reduced carbamoyl methyl viologen as cosubstrate
50.4 - 78
3-hydroxybenzoate
44.9
3-Methoxybenzoate
-
-
6.1 - 12.8
3-methylbenzoate
8
4-(hydroxymethyl)benzoate
-
with reduced carbamoyl methyl viologen as cosubstrate
1 - 1.2
4-Chlorobenzoate
1.4
4-Fluorobenzoate
-
-
3
4-hydroxy-3-methoxybenzaldehyde
-
4-methylbenzoate, with reduced carbamoyl methyl viologen as cosubstrate; with carbamoyl methyl viologen as cosubstrate
12
4-hydroxybenzaldehyde
-
with carbamoyl methyl viologen as cosubstrate
130 - 382
4-hydroxybenzoate
0.005
4-methoxybenzaldehyde
-
terephthalaldehyde, with carbamoyl methyl viologen as cosubstrate; with carbamoyl methyl viologen as cosubstrate
2.1
4-Methoxybenzoate
-
-
5
4-Methylbenzoate
-
-
0.1
5-Phenyl-2,4-pentadienate
-
with reduced carbamoyl methyl viologen as cosubstrate
0.0125 - 0.019
acetaldehyde
1.8 - 5.6
acetate
0.0014 - 0.057
benzaldehyde
16.7 - 53
Benzoate
0.169 - 0.55
benzyl viologen
0.002 - 0.022
Butanal
0.8
Butanoate
-
-
0.012
Butyraldehyde
-
-
0.012
cinnamaldehyde
-
with carbamoyl methyl viologen as cosubstrate
1.7
cinnamate
-
with reduced carbamoyl methyl viologen as cosubstrate
0.04 - 0.136
crotonaldehyde
0.016
DL-glyceraldehyde
-
-
0.01
ES-1 ferredoxin
-
0.0308
furfural
-
with benzyl viologen as cosubstrate
0.084
Glutaraldehyde
-
-
0.196
glyceraldehyde
-
with benzyl viologen as cosubstrate, at 45°C
0.05
Indoleacetaldehyde
0.028 - 0.033
Isovaleraldehyde
1.422 - 1.6
methanal
2.9
methyl viologen
0.067 - 0.076
phenylacetaldehyde
0.0055 - 0.15
propanal
6.3 - 6.4
propanoate
0.017
propionaldehyde
-
-
0.03 - 0.16
reduced carbamoyl methyl viologen
0.065
Salicylaldehyde
-
with benzyl viologen as cosubstrate, at 85°C
4
terephthalate
-
with reduced carbamoyl methyl viologen as cosubstrate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.6 - 343
acetaldehyde
1.25 - 720
benzaldehyde
250
benzyl viologen
Thermococcus sp.
-
with crotonaldehyde as cosubstrate, at 85°C
22 - 269
crotonaldehyde
1.19 - 1.22
decylaldehyde
270
ES-1 ferredoxin
Thermococcus sp.
-
with crotonaldehyde as cosubstrate, at 85°C
-
10.5
glyceraldehyde
Thermococcus sp.
-
with benzyl viologen as cosubstrate, at 45°C
55
indolecetaldehyde
Thermococcus sp.
-
with benzyl viologen as cosubstrate, at 85°C
272
Isovaleraldehyde
Thermococcus sp.
-
with benzyl viologen as cosubstrate, at 85°C
950
methanal
Thermococcus sp.
-
with benzyl viologen as cosubstrate, at 85°C
62
methyl viologen
Thermococcus sp.
-
with crotonaldehyde as cosubstrate, at 85°C
0.8 - 1.2
octaldehyde
960
phenylacetaldehyde
Thermococcus sp.
-
with benzyl viologen as cosubstrate, at 85°C
1100
propanal
Thermococcus sp.
-
with benzyl viologen as cosubstrate, at 85°C
13
Salicylaldehyde
Thermococcus sp.
-
with benzyl viologen as cosubstrate, at 85°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
19.6
-
34°C, pH 8.5
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.1
-
4-fluorobenzoate
4.4 - 4.7
-
benzoate and reduced carbamoyl methyl viologen as substrate
4.7
-
4-methoxybenzoate; 4-methoxybenzoate and reduced carbamoyl methyl viologen as substrate; propanoate and reduced carbamoyl methyl viologen as substrate
9
-
butanal and NH2-CO-methyl viologen as substrates
11
-
activity increases up to pH 11
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3.9 - 4.1
-
pH 3.9: 80% of maximal activity, pH 4.1: optimum, 4-fluorobenzoate and reduced carbamoyl methyl viologen as substrates
3.9 - 4.7
-
pH 3.9: 55% of maximal activity, pH 4.3-4.7: optimum; pH 3.9: 55% of maximal activity, pH 4.7: optimum, 4-methoxybenzoate and reduced carbamoyl methyl viologen as substrates
4.7 - 5.5
-
pH 4.7: optimum, pH 5.5: 20% of maximal activity, propanoate reduced carbamoyl methyl viologen as substrates
6 - 7
-
pH 6.0: optimum, pH 7.0: 25% of maximal activity, reduction of propanoate or benzoate
8 - 10
-
about 90% of maximal activity, butanal and NH2-CO-methyl viologen as substrates
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
-
aldehyde dehydrogenation
46
-
at pH 4.5
48
-
and above
51
-
propanoate as substrate, pH 4.8
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 50
-
60% of maximal activity at 30°C and 50°C, inactive at 60°C, aldehyde dehydrogenation
51 - 71
-
51°C: optimum, 71°C: about 60% of maximal activity, propanoate and reduced carbamoyl methyl viologen as substrates
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
activity in the crude extract is about 100times increased if 0.010 mM tungstate and a sulfur source in adition to sulfate is given to the growth medium
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
may catalyze reaction of substrates incorporated into a cell membrane
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
14000
-
1 * 14000, beta, + 1 * 64000, alpha, enzyme exists in a dimeric and a heptameric form, SDS-PAGE; 3 * 14000, + 1 * 43000, gamma, + 3 * 64000, alpha, enzyme exists in a dimeric and a heptameric form, SDS-PAGE
43000
-
3 * 14000, + 1 * 43000, gamma, + 3 * 64000, alpha, enzyme exists in a dimeric and a heptameric form, SDS-PAGE
62000
-
2 * 62000, SDS-PAGE
64000
-
1 * 14000, beta, + 1 * 64000, alpha, enzyme exists in a dimeric and a heptameric form, SDS-PAGE; 3 * 14000, + 1 * 43000, gamma, + 3 * 64000, alpha, enzyme exists in a dimeric and a heptameric form, SDS-PAGE
65000
-
gel filtration
86000
-
dimeric form: alpha,beta, gel filtration
105000
-
gel filtration
120000 - 126000
-
gel filtration
125000
-
gel filtration
220000 - 260000
-
gel filtration
300000
-
heptameric form: alpha3,beta3,gamma, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
heptamer
-
3 * 14000, + 1 * 43000, gamma, + 3 * 64000, alpha, enzyme exists in a dimeric and a heptameric form, SDS-PAGE
monomer
-
1 * 67000, SDS-PAGE
additional information
-
enzyme is a homodimeric protein of 200 kDa which can dissociate to stable monomers when encapsulated in reverse micelles, sedimentation studies
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65
-
decrease of activity after 3 min
70
-
enzyme concentration 2.0 mg/ml, 50% loss of activity after 5 min
85
-
enzyme concentration 2.0 mg/ml, 50% loss of activity after 1 min
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
22% loss of activity after 5 min in air, at 4°C
-
11943
90% loss of activity after 10 min exposure to air
-
11938
extremely labile in presence of O2, 40% loss of activity after 2 min when stirred in air
-
11937
extremely sensitive to inactivation by O2. The extent of inactivation is greatly dependent on the temperature of incubation
-
11935
the tungsten-containing enzyme is very sensitive to O2 especially in the reduced state, the reduced enzyme loses 80% of the activity after 10 min. The molybdenum-containing enzyme shows only moderate O2 sensitivity
-
11940
unstable to air
-
11936
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
using strict anaerobic conditions
-