Information on EC 1.2.1.32 - aminomuconate-semialdehyde dehydrogenase

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

EC NUMBER
COMMENTARY hide
1.2.1.32
-
RECOMMENDED NAME
GeneOntology No.
aminomuconate-semialdehyde dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2-aminomuconate 6-semialdehyde + NAD+ + H2O = 2-aminomuconate + NADH + 2 H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
-
-
-
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reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2-amino-3-carboxymuconate semialdehyde degradation to 2-oxopentenoate
-
-
2-amino-3-carboxymuconate semialdehyde degradation to glutaryl-CoA
-
-
2-aminophenol degradation
-
-
2-nitrobenzoate degradation I
-
-
4-chloronitrobenzene degradation
-
-
4-nitrotoluene degradation II
-
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tryptophan metabolism
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Tryptophan metabolism
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-
SYSTEMATIC NAME
IUBMB Comments
2-aminomuconate-6-semialdehyde:NAD+ 6-oxidoreductase
Also acts on 2-hydroxymuconate semialdehyde.
CAS REGISTRY NUMBER
COMMENTARY hide
37250-95-6
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
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Manually annotated by BRENDA team
; Bordetella sp. strain 10d
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
formerly Pseudomonas cepacia
SwissProt
Manually annotated by BRENDA team
basonym Alcaligenes eutrophus, strain 335
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-
Manually annotated by BRENDA team
MSO22
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-
Manually annotated by BRENDA team
MSO22
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-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
grown on nitrobenzene
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-
Manually annotated by BRENDA team
grown on nitrobenzene
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-
Manually annotated by BRENDA team
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
grown on phenol or cresols
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-aminomuconate 6-semialdehyde + NAD+ + H2O
2-aminomuconate + NADH + 2 H+
show the reaction diagram
2-aminomuconate 6-semialdehyde + NAD+ + H2O
2-aminomuconate + NADH + H+
show the reaction diagram
2-aminomuconate-6-semialdehyde + NAD+ + H2O
2-aminomuconate + NADH
show the reaction diagram
2-aminomuconic acid semialdehyde + NAD+ + H2O
2-aminomuconate + NADH + H+
show the reaction diagram
-
-
-
-
?
2-fluorobenzaldehyde + NAD+ + H2O
2-fluorobenzoate + NADH + H+
show the reaction diagram
2-hydroxy-5-methyl-6-oxohexa-2,4-dienoate + NAD+ + H2O
2-hydroxy-5-methylmuconate + NADH
show the reaction diagram
2-hydroxy-5-methyl-muconic-6-semialdehyde + NAD+
2-hydroxy-5-methylmuconate + NADH
show the reaction diagram
2-hydroxymuconate-6-semialdehyde + NAD+ + H2O
2-hydroxymuconate + NADH
show the reaction diagram
2-hydroxymuconate-6-semialdehyde + NAD+ + H2O
4-oxalocrotonate + NADH + H+
show the reaction diagram
2-hydroxymuconic 6-semialdehyde + NAD+ + H2O
2-hydroxymuconate + NADH + H+
show the reaction diagram
-
substrate for spectrophotometric activity assay, relative activity 100%
-
-
?
2-hydroxymuconic acid semialdehyde + NAD+ + H2O
2-hydroxymuconate + NADH + H+
show the reaction diagram
3-chlorobenzaldehyde + NAD+ + H2O
3-chlorobenzoate + NADH
show the reaction diagram
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low activity
-
-
?
3-fluorobenzaldehyde + NAD+ + H2O
3-fluorobenzoate + NADH + H+
show the reaction diagram
-
low activity
-
-
?
3-methoxybenzaldehyde + NAD+ + H2O
3-methoxybenzoate + NADH
show the reaction diagram
-
low activity
-
-
?
3-methylbenzaldehyde + NAD+ + H2O
3-methylbenzoate + NADH
show the reaction diagram
-
low activity
-
-
?
3-nitrobenzaldehyde + NAD+ + H2O
3-nitrobenzoate + NADH
show the reaction diagram
4-carboxybenzaldehyde + NAD+ + H2O
4-carboxybenzoate + NADH
show the reaction diagram
-
-
-
-
?
4-chlorobenzaldehyde + NAD+ + H2O
4-chlorobenzoate + NADH
show the reaction diagram
4-fluorobenzaldehyde + NAD+ + H2O
4-fluorobenzoate + NADH + H+
show the reaction diagram
4-methoxybenzaldehyde + NAD+ + H2O
4-methoxybenzoate + NADH + H+
show the reaction diagram
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low activity
-
-
?
4-methylbenzaldehyde + NAD+ + H2O
4-methylbenzoate + NADH
show the reaction diagram
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low activity
-
-
?
4-nitrobenzaldehyde + NAD+ + H2O
4-nitrobenzoate + NADH + H+
show the reaction diagram
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low activity
-
-
?
5-chloro-2-hydroxymuconic-6-semialdehyde + NAD+
5-chloro-2-hydroxymuconate + NADH
show the reaction diagram
acetaldehyde + NAD+ + H2O
acetate + NADH + H+
show the reaction diagram
benzaldehyde + NAD+ + H2O
benzoate + NADH + H+
show the reaction diagram
butyraldehyde + NAD+ + H2O
butyrate + NADH + H+
show the reaction diagram
crotonaldehyde + NAD+ + H2O
crotonate + NADH
show the reaction diagram
formaldehyde + NAD+ + H2O
formate + NADH
show the reaction diagram
formaldehyde + NAD+ + H2O
formate + NADH + H+
show the reaction diagram
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relative activity 16,5%
-
-
?
hexaldehyde + NAD+ + H2O
n-hexanoic acid + NADH
show the reaction diagram
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low activity
-
-
?
n-butanal + NAD+ + H2O
n-butanoate + NADH + H+
show the reaction diagram
propanal + NAD+ + H2O
n-propanoate + NADH + H+
show the reaction diagram
propionaldehyde + NAD+ + H2O
propionate + NADH + H+
show the reaction diagram
pyridine 4-carboxyaldehyde + NAD+ + H2O
pyridine 4-carboxylate + NADH
show the reaction diagram
-
-
-
-
?
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
2-aminomuconate 6-semialdehyde + NAD+ + H2O
2-aminomuconate + NADH + 2 H+
show the reaction diagram
2-aminomuconate 6-semialdehyde + NAD+ + H2O
2-aminomuconate + NADH + H+
show the reaction diagram
2-aminomuconate-6-semialdehyde + NAD+ + H2O
2-aminomuconate + NADH
show the reaction diagram
2-hydroxymuconate-6-semialdehyde + NAD+ + H2O
2-hydroxymuconate + NADH
show the reaction diagram
-
-
-
-
?
2-hydroxymuconate-6-semialdehyde + NAD+ + H2O
4-oxalocrotonate + NADH + H+
show the reaction diagram
2-hydroxymuconic acid semialdehyde + NAD+ + H2O
2-hydroxymuconate + NADH + H+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-Chlorobenzaldehyde
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competitive
2-Methoxybenzaldehyde
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competitive
CuSO4
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0% remaining activity at an inhibitor concentration of 1 mM; 100% inhibtion at 1 mM
HgCl2
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0% remaining activity at an inhibitor concentration of 1 mM; 100% inhibtion at 1 mM
iodoacetamide
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equimolar amount reduces benzaldehyde oxidation activity by 44%
iodoacetic acid
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31% inhibtion at 1 mM; 69% remaining activity at an inhibitor concentration of 1 mM
N-ethylmaleimide
N-Methylmaleimide
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82% inhibtion at 1 mM
p-chloromercuribenzoate
p-chloromercuribenzoic acid
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41% remaining activity at an inhibitor concentration of 1 mM; 59% inhibtion at 1 mM
ZnSO4
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26% remaining activity at an inhibitor concentration of 1 mM; 74% inhibtion at 1 mM
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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HMSD in crude extracts prepared from pDTG912/B shows higher activity in potassium phosphate buffer than in Tris-HCl buffer (50 mM)
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2
2-Fluorobenzaldehyde
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-
0.0093
2-hydroxy-5-methyl-6-oxohexa-2,4-dienoate
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synonym 5-methyl-2-hydroxymuconic-6-semialdehyde
0.002
2-hydroxy-5-methyl-muconic-6-semialdehyde
pH 8.5, 25°C
0.011 - 0.026
2-hydroxymuconate-6-semialdehyde
0.48
2-nitrobenzaldehyde
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1.3
3-Chlorobenzaldehyde
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0.17
3-Fluorobenzaldehyde
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0.94
3-Methoxybenzaldehyde
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-
0.63
3-methylbenzaldehyde
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-
0.81
3-Nitrobenzaldehyde
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-
0.7
4-Chlorobenzaldehyde
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-
0.31
4-Fluorobenzaldehyde
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-
1.1
4-methoxybenzaldehyde
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-
0.53
4-methylbenzaldehyde
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-
0.31
4-Nitrobenzaldehyde
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-
0.083
5-chloro-2-hydroxymuconic-6-semialdehyde
pH 8.5, 25°C
0.46
benzaldehyde
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-
0.019 - 1.316
NAD+
additional information
additional information
Michaelis-Menten steady-state kinetics and kinetic analysis, overview
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
99300
2-hydroxy-5-methyl-muconic-6-semialdehyde
pH 8.5, 25°C
21900
2-hydroxymuconate-6-semialdehyde
pH 8.5, 25°C
2300
5-chloro-2-hydroxymuconic-6-semialdehyde
pH 8.5, 25°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.13
2-Chlorobenzaldehyde
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-
0.06
2-Methoxybenzaldehyde
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-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0037
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after streptomycin sulfate treatment
0.0041
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cell extract
0.0092
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after ammonium sulfate precipitation
0.046
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after DE52 chromatography
0.071
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after DEAE-Toyopearl chromatography
0.075
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after DEAE-Cellulofine chromatography
0.0765
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-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.3
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2-aminomuconic acid oxidation
7.5 - 8
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9.6
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benzaldehyde oxidation
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 9
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more than 50% of maximal activity between pH 7 and 9
8 - 11
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benzaldehyde oxidation, more than 50% of maximal activity between pH 8 and 11
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
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assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.61
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calculated
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
51504
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x * 51504, nucleotide sequence
51682
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x * 51682, nucleotide sequence
51700
-
x * 51700, nucleotide sequence
51740
calculated from the predicted amino acid sequence
52300
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sequence analysis
57800
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3 * 57000, SDS-PAGE, 3 * 57800, nucleotide sequence
126000
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gel filtration
160000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
trimer
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purified recombinant His-tagged E268A mutant enzyme in complex with NAD+ or NAD+ and 2-aminomuconate or 2-hydroxymuconate, hanging drop diffusion, mixing of 0.0015 ml of 40 mg/ml protein solution with 0.0015 ml of reservoir solution containing 20% PEG 3350 and 0.2 M sodium phosphate dibasic monohydrate, pH 9.1, at 18°C, 2-3 days, crystals are soaked in ligand solution for the formation of complex crystals, X-ray diffraction structure determination and analysis at 1.95-2.20 A resolution, molecular replacement using 5-carboxymethyl-2-hydroxymuconate semialdehyde dehydrogenase, PDB: 2D4E, as a search model, and molecular modelling
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-10°C, 1 week, 50% loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate fractionation, chromatography on DE52 cellulose, chromatography on DEAE-cellulofine, chromatography on DEAE-toyopearl; ammonium sulfate precipitation followed by 3 chromatography steps
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by nickelnitrilotriacetic acid affinity chromatography; Ni-affinity chromatography
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erroneous identification as benzaldehyde dehydrogenase corrected
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erroneously identified as benzaldehyde dehydrogenase
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partial
recombinant N-terminally His-tagged wild-type and mutant enzymes from Escherichia coli
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli carrying pDTG912, pDTG912/A, and pDTG912/B
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expressed in Escherichia coli HB101
expression as His-tag fusion protein in Escherichia coli Tuner (DE3); into the plasmid pDESTF1, which encodes an N-terminal six-His tag and is under control of the T7lac promoter, is used to transform Escherichia coli Tuner DE3
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gene dmpC
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gene hpcC
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gene phnG
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gene xylG from TOL plasmid of strain mt-2
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NAH plasmid of Pseudomonas putida, carrying the coding gene nahI, cloned into Escherichia coli
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recombinant expressin of N-terminally His-tagged wild-type and mutant enzymes in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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codG encoding 2-hydroxymuconic semialdehyde dehydrogenase shows a higher degree of similarity to those genes in classical bacteria
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