Information on EC 1.1.1.312 - 2-hydroxy-4-carboxymuconate semialdehyde hemiacetal dehydrogenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.312
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RECOMMENDED NAME
GeneOntology No.
2-hydroxy-4-carboxymuconate semialdehyde hemiacetal dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4-carboxy-2-hydroxymuconate semialdehyde hemiacetal + NADP+ = 2-oxo-2H-pyran-4,6-dicarboxylate + NADPH + 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
Aminobenzoate degradation
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Benzoate degradation
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protocatechuate degradation I (meta-cleavage pathway)
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Tyrosine metabolism
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SYSTEMATIC NAME
IUBMB Comments
4-carboxy-2-hydroxymuconate semialdehyde hemiacetal:NADP+ 2-oxidoreductase
The enzyme does not act on unsubstituted aliphatic or aromatic aldehydes or glucose; NAD+ can replace NADP+, but with lower affinity. The enzyme was initially believed to act on 4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde and produce 4-carboxy-2-hydroxy-cis,cis-muconate [1]. However, later studies showed that the substrate is the hemiacetal form [3], and the product is 2-oxo-2H-pyran-4,6-dicarboxylate [2,4].
CAS REGISTRY NUMBER
COMMENTARY hide
67272-39-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain SYK-6; SYK-6
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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
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NAD+
4-carboxy-2-hydroxy-cis,cis-muconate + NADH
show the reaction diagram
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH
show the reaction diagram
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+ + H2O
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH + 2 H+
show the reaction diagram
4-carboxy-2-hydroxymuconate semialdehyde + NADP+
2-pyrone-4,6-dicarboxylic acid + NADPH + H2O
show the reaction diagram
protocatechuate + NADP+ + H2O
2-pyrone-4,6-dicarboxylic acid + NADPH + H+
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
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+ + H2O
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH + 2 H+
show the reaction diagram
additional information
?
-
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2-pyrone-4,6-dicarboxylic acid may be a metabolic intermediate in the bacterial metabolism of protocatechuic acid
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-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-pyrone-4,6-dicarboxylic acid
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non-competitive inhibition with respect to 4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
5,5'-dithiobis(2-nitrobenzoate)
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1 h at 0.1 mM inhibits 98% of enzyme activity
Blue dextran
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competitive inhibitor with respect to NADP+
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HgCl2
methoxy Reactive Blue 2
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inhibits the enzyme non-competitively with respect to 4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde and competitively with respect to NADP+
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Monoiodoacetic acid
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weaker inhibitor than p-chloromercuribenzoate or HgCl2
N-ethylmaleimide
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weaker inhibitor than p-chloromercuribenzoate or HgCl2
NADH
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competitive inhibition with respect to NAD+, non-competitive inhibition with respect to 4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
NADPH
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competitive inhibition with respect to NADP, non-competitive inhibition with respect to 4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
p-chloromercuribenzoate
Reactive blue 2
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inhibits the enzyme non-competitively with respect to 4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde and competitively with respect to NADP+
Reactive Blue 4
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inhibits the enzyme non-competitively with respect to 4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde and competitively with respect to NADP+
additional information
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not: various metal ions, metal chelating reagents, reducing reagents
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Lubrol
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the enzyme activity increases in a sigmoidal manner with increasing concentrations, minimum concentration necessary for the increase of enzyme activity is higher than 0.05 mM, effectively eliminates the dye inhibition
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.02 - 0.075
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
0.252 - 0.284
NAD+
0.0061 - 0.314
NADP+
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00006
Blue dextran
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-
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0.0002
methoxy Reactive Blue 2
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coenzyme NADP+, similar value with coenzyme NAD+
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0.0002 - 0.072
Reactive blue 2
0.0045
Reactive Blue 4
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coenzyme NADP+, similar value with coenzyme NAD+
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
360
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after purification from the cell extract of Escherichia coli
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5
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fermenter condition for production of 2-pyrone-4,6-dicarboxylic acid, PDC
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 9.3
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at pH 5.5 and 9.3: about 50% of activity maximum
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34590
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1 * 34590, amino acid sequence
35000
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2 * 35000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 7
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highest stability
288243
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
42
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10 min, pH 7.0, 50% loss of activity
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, for at least 4 months
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
from the cell extract of Escherichia coli, using POROS polyethyleneimine anion-exchange chromatography, POROS quaternized PI anion-exchange chromatography and POROS phenylether hydrophobic-interaction chromatography
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recombinant enzyme expressed in Escherichia coli
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using gel filtration on Sephadex G-200
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase gene ligC expressed in Escherichia coli
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coexpression with protocatechuate 4,5-dioxygenase in Pseudomonas putida PpY1100; into the pKT230MC vector for expression in Pseudomonas putida PpY1100 and into pUC119 for DNA amplification in Escherichia coli DH5alpha
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
industry