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
-
-
-
-
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
-
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2-nitrobenzoate degradation I
-
-
4-nitrotoluene degradation II
-
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tryptophan metabolism
-
-
Tryptophan metabolism
-
-
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
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Azotobacter sp.
-
-
-
Manually annotated by BRENDA team
Bordetella sp. strain 10d; strain 10d
-
-
Manually annotated by BRENDA team
strain 10d
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-
Manually annotated by BRENDA team
strain G4, formerly Pseudomonas cepacia
SwissProt
Manually annotated by BRENDA team
strain J2315
-
-
Manually annotated by BRENDA team
basonym Alcaligenes eutrophus, strain 335
-
-
Manually annotated by BRENDA team
RB1
-
-
Manually annotated by BRENDA team
MSO22
-
-
Manually annotated by BRENDA team
MSO22
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain JS45 grown on nitrobenzene
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-
Manually annotated by BRENDA team
strain JS45 grown on nitrobenzene
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-
Manually annotated by BRENDA team
Pseudomonas putida NCIB 10015
strain NCIB 10015 grown on phenol or cresols
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-
Manually annotated by BRENDA team
strain CF600
-
-
Manually annotated by BRENDA team
-
-
-
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-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
-
low activity
-
-
?
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
-
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
-
low activity
-
-
?
4-fluorobenzaldehyde + NAD+ + H2O
4-fluorobenzoate + NADH + H+
show the reaction diagram
-
low activity
-
-
?
4-methoxybenzaldehyde + NAD+ + H2O
4-methoxybenzoate + NADH + H+
show the reaction diagram
-
low activity
-
-
?
4-methylbenzaldehyde + NAD+ + H2O
4-methylbenzoate + NADH
show the reaction diagram
-
low activity
-
-
?
4-nitrobenzaldehyde + NAD+ + H2O
4-nitrobenzoate + NADH + H+
show the reaction diagram
-
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
-
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
?
-
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 + 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
-
0% remaining activity at an inhibitor concentration of 1 mM; 100% inhibtion at 1 mM
HgCl2
-
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
-
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
-
-
0.0093
2-hydroxy-5-methyl-6-oxohexa-2,4-dienoate
-
synonym 5-methyl-2-hydroxymuconic-6-semialdehyde
0.002
2-hydroxy-5-methyl-muconic-6-semialdehyde
pH 8.5, 25C
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
-
-
0.53
4-methylbenzaldehyde
-
-
0.31
4-Nitrobenzaldehyde
-
-
0.083
5-chloro-2-hydroxymuconic-6-semialdehyde
pH 8.5, 25C
0.46
benzaldehyde
-
-
0.019 - 1.316
NAD+
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
99300
2-hydroxy-5-methyl-muconic-6-semialdehyde
Burkholderia cepacia
Q83XU8
pH 8.5, 25C
21900
2-hydroxymuconate-6-semialdehyde
Burkholderia cepacia
Q83XU8
pH 8.5, 25C
2300
5-chloro-2-hydroxymuconic-6-semialdehyde
Burkholderia cepacia
Q83XU8
pH 8.5, 25C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.13
2-Chlorobenzaldehyde
-
-
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
-
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
51740
calculated from the predicted amino acid sequence
52300
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sequence analysis
57000
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SDS-PAGE; SDS-PAGE, recombinant protein
126000
-
gel filtration
160000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 57000, SDS-PAGE
trimer
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-10C, 1 week, 50% loss of activity
-
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
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli carrying pDTG912, pDTG912/A, and pDTG912/B
-
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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
codG encoding 2-hydroxymuconic semialdehyde dehydrogenase shows a higher degree of similarity to those genes in classical bacteria