Information on EC 1.2.1.85 - 2-hydroxymuconate-6-semialdehyde dehydrogenase

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 enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.2.1.85
-
RECOMMENDED NAME
GeneOntology No.
2-hydroxymuconate-6-semialdehyde dehydrogenase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2-hydroxymuconate-6-semialdehyde + NAD+ + H2O = (2Z,4E)-2-hydroxyhexa-2,4-dienedioate + NADH + 2 H+
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2,3-dihydroxybenzoate degradation
-
-
4-amino-3-hydroxybenzoate degradation
-
-
Benzoate degradation
-
-
catechol degradation to 2-oxopent-4-enoate II
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
protocatechuate degradation III (para-cleavage pathway)
-
-
Xylene degradation
-
-
phenol degradation
-
-
SYSTEMATIC NAME
IUBMB Comments
2-hydroxymuconate-6-semialdehyde:NAD+ oxidoreductase
This substrate for this enzyme is formed by meta ring cleavage of catechol (EC 1.13.11.2, catechol 2,3-dioxygenase), and is an intermediate in the bacterial degradation of several aromatic compounds. Has lower activity with benzaldehyde [1]. Activity with NAD+ is more than 10-fold higher than with NADP+ [3]. cf. EC 1.2.1.32, aminomuconate-semialdehyde dehydrogenase.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
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-hydroxy-5-methyl-6-oxohexa-2,4-dienoate + NAD+ + H2O
(2E,4Z)-2-hydroxy-5-methylhexa-2,4-diendioate + NADH + H+
show the reaction diagram
-
-
-
-
?
2-hydroxymuconate-6-semialdehyde + NAD+ + H2O
(2Z,4E)-2-hydroxyhexa-2,4-dienedioate + NADH + H+
show the reaction diagram
3-chlorobenzaldehyde + NAD+ + H2O
3-chlorobenzoate + NADH + H+
show the reaction diagram
-
-
-
-
?
3-fluorobenzaldehyde + NAD+ + H2O
3-fluorobenzoate + NADH + H+
show the reaction diagram
-
-
-
-
?
3-methoxybenzaldehyde + NAD+ + H2O
3-methoxybenzoate + NADH + H+
show the reaction diagram
-
-
-
-
?
3-methylbenzaldehyde + NAD+ + H2O
3-methylbenzoate + NADH + H+
show the reaction diagram
-
-
-
-
?
3-nitrobenzaldehyde + NAD+ + H2O
3-nitrobenzoate + NADH + H+
show the reaction diagram
-
-
-
-
?
4-methylbenzaldehyde + NAD+ + H2O
4-methylbenzoate + NADH + H+
show the reaction diagram
-
-
-
-
?
5-chloro-2-hydroxymuconic semialdehyde + NAD+ + H2O
5-chloro-2-hydroxymuconic acid + NADH + H+
show the reaction diagram
acetaldehyde + NAD+ + H2O
acetate + NADH + H+
show the reaction diagram
-
113% activity compared to 2-hydroxymuconate-6-semialdehyde
-
-
?
benzaldehyde + NAD+ + H2O
benzoate + NADH + H+
show the reaction diagram
butyraldehyde + NAD+ + H2O
butanoate + NADH + H+
show the reaction diagram
-
138% activity compared to 2-hydroxymuconate-6-semialdehyde
-
-
?
formaldehyde + NAD+ + H2O
formate + NADH + H+
show the reaction diagram
-
16.5% activity compared to 2-hydroxymuconate-6-semialdehyde
-
-
?
propionaldehyde + NAD+ + H2O
propanoate + NADH + H+
show the reaction diagram
-
107% activity compared to 2-hydroxymuconate-6-semialdehyde
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD+
-
highly specific for NAD+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Cu2+
-
complete inhibition at 1 mM
Hg2+
-
complete inhibition at 1 mM
iodoacetic acid
-
69% residual activity at 1 mM
N-ethylmaleimide
-
18% residual activity at 1 mM
p-chloromercuribenzoate
-
41% residual activity at 1 mM
Zn2+
-
26% residual activity at 1 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0093
2-hydroxy-5-methyl-6-oxohexa-2,4-dienoate
-
in 100 mM Tris-HCl, pH 8.5, at 25C
0.017
2-hydroxymuconate-6-semialdehyde
-
in 100 mM Tris-HCl, pH 8.5, at 25C
1.3
3-Chlorobenzaldehyde
-
in 100 mM glycine-NaOH (pH 9.2), at 25C
0.17
3-Fluorobenzaldehyde
-
in 100 mM glycine-NaOH (pH 9.2), at 25C
0.94
3-Methoxybenzaldehyde
-
in 100 mM glycine-NaOH (pH 9.2), at 25C
0.63
3-methylbenzaldehyde
-
in 100 mM glycine-NaOH (pH 9.2), at 25C
0.81
3-Nitrobenzaldehyde
-
in 100 mM glycine-NaOH (pH 9.2), at 25C
0.53
4-methylbenzaldehyde
-
in 100 mM glycine-NaOH (pH 9.2), at 25C
0.46
benzaldehyde
-
in 100 mM glycine-NaOH (pH 9.2), at 25C
0.33
NAD+
-
in the presence of benzaldehyde, 100 mM glycine-NaOH (pH 9.2), at 25C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2100
2-hydroxy-5-methyl-6-oxohexa-2,4-dienoate
Pseudomonas putida
-
apparent value, in 100 mM Tris-HCl, pH 8.5, at 25C
16599
1600
2-hydroxymuconate-6-semialdehyde
Pseudomonas putida
-
apparent value, in 100 mM Tris-HCl, pH 8.5, at 25C
5232
22
3-Chlorobenzaldehyde
Pseudomonas putida
-
apparent value, in 100 mM glycine-NaOH (pH 9.2), at 25C
2459
330
3-Fluorobenzaldehyde
Pseudomonas putida
-
apparent value, in 100 mM glycine-NaOH (pH 9.2), at 25C
3968
8
3-Methoxybenzaldehyde
Pseudomonas putida
-
apparent value, in 100 mM glycine-NaOH (pH 9.2), at 25C
1856
36
3-methylbenzaldehyde
Pseudomonas putida
-
apparent value, in 100 mM glycine-NaOH (pH 9.2), at 25C
2710
20
3-Nitrobenzaldehyde
Pseudomonas putida
-
apparent value, in 100 mM glycine-NaOH (pH 9.2), at 25C
2537
10
4-methylbenzaldehyde
Pseudomonas putida
-
apparent value, in 100 mM glycine-NaOH (pH 9.2), at 25C
2073
32
benzaldehyde
Pseudomonas putida
-
apparent value, in 100 mM glycine-NaOH (pH 9.2), at 25C
146
56
NAD+
Pseudomonas putida
-
apparent value, in the presence of benzaldehyde, 100 mM glycine-NaOH (pH 9.2), at 25C
7
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
enzyme from cell extract shows a specific activity of 0.0041 units/mg in 100 mM sodium phosphate, pH 7.5, at 24C. After 17fold purification, the enzyme shows a specific activity of 0.071 units/mg in 100 mM sodium phosphate, pH 7.5, at 24C, in 100 mM sodium phosphate, pH 7.5, at 24C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.3
-
pH optimum for the oxidation of 2-hydroxymuconic semialdehyde
9.6
-
pH optimum for the oxidation of benzaldehyde
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
53188
-
x * 53188, calculated from amino acid sequence
58000
-
x * 58000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate fractionation, TSKgel DEAE-5PW column chromatography, Affigel-Blue affinity chromatography, and TSKgel Phenyl-5PW column chromatography
-
streptomycin sulfate precipitation, ammonium sulfate precipitation, DE52 cellulose column chromatography, DEAE-cellulofine column chromatography, and DEAE-Toyopearl column chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
-