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IUBMB Comments 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 . However, later studies showed that the substrate is the hemiacetal form , and the product is 2-oxo-2H-pyran-4,6-dicarboxylate [2,4].
The expected taxonomic range for this enzyme is: Bacteria, Archaea
Synonyms
2-hydroxy-4-carboxymuconate 6-semialdehyde dehydrogenase, 2-hydroxy-4-carboxymuconate-6-semialdehyde dehydrogenase, 4-carboxy-2-hydroxy-cis,cis-muconate-6-semialdehyde:NADP+ oxidoreductase, 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase, alpha-hydroxy-gamma-carboxymuconic epsilon-semialdehyde dehydrogenase, CHMS dehydrogenase, CHMS hydrolase, dehydrogenase, 2-hydroxy-4-carboxymuconate 6-semialdehyde,
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2-hydroxy-4-carboxymuconate 6-semialdehyde dehydrogenase
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2-hydroxy-4-carboxymuconate-6-semialdehyde dehydrogenase
4-carboxy-2-hydroxy-cis,cis-muconate-6-semialdehyde:NADP+ oxidoreductase
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4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase
alpha-hydroxy-gamma-carboxymuconic epsilon-semialdehyde dehydrogenase
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dehydrogenase, 2-hydroxy-4-carboxymuconate 6-semialdehyde
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2-hydroxy-4-carboxymuconate-6-semialdehyde dehydrogenase
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2-hydroxy-4-carboxymuconate-6-semialdehyde dehydrogenase
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2-hydroxy-4-carboxymuconate-6-semialdehyde dehydrogenase
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4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase
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4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase
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4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase
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CHMS dehydrogenase
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CHMS hydrolase
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4-carboxy-2-hydroxymuconate semialdehyde hemiacetal + NADP+ = 2-oxo-2H-pyran-4,6-dicarboxylate + NADPH + H+
4-carboxy-2-hydroxymuconate semialdehyde hemiacetal + NADP+ = 2-oxo-2H-pyran-4,6-dicarboxylate + NADPH + H+
ordered bi-bi mechanism
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4-carboxy-2-hydroxymuconate semialdehyde hemiacetal + NADP+ = 2-oxo-2H-pyran-4,6-dicarboxylate + NADPH + H+
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reduction
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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].
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NAD+
4-carboxy-2-hydroxy-cis,cis-muconate + NADH
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+ + H2O
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH + 2 H+
4-carboxy-2-hydroxymuconate semialdehyde + NADP+
2-pyrone-4,6-dicarboxylic acid + NADPH + H2O
protocatechuate + NADP+ + H2O
2-pyrone-4,6-dicarboxylic acid + NADPH + H+
additional information
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NAD+
4-carboxy-2-hydroxy-cis,cis-muconate + NADH
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NAD+
4-carboxy-2-hydroxy-cis,cis-muconate + NADH
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NAD+ is less effective than NADP+
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NAD+
4-carboxy-2-hydroxy-cis,cis-muconate + NADH
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NAD+ is less effective than NADP+
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NAD+
4-carboxy-2-hydroxy-cis,cis-muconate + NADH
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NAD+
4-carboxy-2-hydroxy-cis,cis-muconate + NADH
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH
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following intramolecular dehydrogenation to the lactone 2-pyrone-4,6-dicarboxylic acid
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH
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following intramolecular dehydrogenation to the lactone 2-pyrone-4,6-dicarboxylic acid, it is not clear whether the lactonization occurs enzymatically or nonenzymatically
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH
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or NAD+
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH
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NAD+ is less effective than NADP+
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH
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NAD+ is less effective than NADP+
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH
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following intramolecular dehydrogenation to the lactone 2-pyrone-4,6-dicarboxylic acid
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH
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following intramolecular dehydrogenation to the lactone 2-pyrone-4,6-dicarboxylic acid
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+ + H2O
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH + 2 H+
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+ + H2O
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH + 2 H+
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4-carboxy-2-hydroxymuconate semialdehyde + NADP+
2-pyrone-4,6-dicarboxylic acid + NADPH + H2O
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4-carboxy-2-hydroxymuconate semialdehyde + NADP+
2-pyrone-4,6-dicarboxylic acid + NADPH + H2O
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protocatechuate + NADP+ + H2O
2-pyrone-4,6-dicarboxylic acid + NADPH + H+
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protocatechuate + NADP+ + H2O
2-pyrone-4,6-dicarboxylic acid + NADPH + H+
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additional information
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not: unsubstituted aliphatic or aromatic aldehydes
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additional information
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interaction with Blue Dextran-2000 and related dyes
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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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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+ + H2O
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH + 2 H+
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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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+ + H2O
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH + 2 H+
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4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde + NADP+ + H2O
4-carboxy-2-hydroxy-cis,cis-muconate + NADPH + 2 H+
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NAD+
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can replace NADP+, but with lower affinity
NAD+
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can replace NADP+, but with lower affinity
NADP+
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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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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+
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
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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HgCl2
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HgCl2
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1 h at 0.01 mM inhibits 83% of enzyme activity
p-chloromercuribenzoate
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p-chloromercuribenzoate
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1 h at 0.01 mM inhibits 78% of enzyme activity
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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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0.02 - 0.075
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
0.02
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
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in the presence of 0.110 mM NADP+
0.0206
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
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in the presence of NAD+
0.026
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
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in the presence of NADP+
0.056
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
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in the presence of 0.110 mM NAD+
0.075
4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde
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25°C
0.252
NAD+
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0.0061
NADP+
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25°C
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0.00006
Blue dextran
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0.0002
methoxy Reactive Blue 2
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coenzyme NADP+, similar value with coenzyme NAD+
0.0002 - 0.072
Reactive blue 2
0.0045
Reactive Blue 4
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coenzyme NADP+, similar value with coenzyme NAD+
0.0002
Reactive blue 2
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coenzyme NADP+, similar value with coenzyme NAD+
0.072
Reactive blue 2
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360
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after purification from the cell extract of Escherichia coli
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6.5
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fermenter condition for production of 2-pyrone-4,6-dicarboxylic acid, PDC
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5.5 - 9.3
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at pH 5.5 and 9.3: about 50% of activity maximum
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NGJ1
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brenda
SYK6
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brenda
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brenda
NGJ1
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brenda
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brenda
SYK-6
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brenda
SYK6
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brenda
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brenda
SYK-6
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brenda
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brenda
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brenda
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34590
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1 * 34590, amino acid sequence
35000
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2 * 35000, SDS-PAGE
67000
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gel filtration
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dimer
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dimer
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2 * 35000, SDS-PAGE
dimer
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2 * 35000, SDS-PAGE
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dimer
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1 * 34590, amino acid sequence
dimer
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1 * 34590, amino acid sequence
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6.5 - 7
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highest stability
288243
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42
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10 min, pH 7.0, 50% loss of activity
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-20°C, for at least 4 months
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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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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
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into the pKT230MC vector for expression in Pseudomonas putida PpY1100 and into pUC119 for DNA amplification in Escherichia coli DH5alpha
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biotechnology
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production of 2-pyrone-4,6-dicarboxylic acid from protocatechuate as a precursor for biopolymers
biotechnology
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production of 2-pyrone-4,6-dicarboxylic acid from protocatechuate as a precursor for biopolymers
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industry
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the authors focus on the metabolic intermediate 2-pyrone-4,6-dicarboxylic acid as a potential raw material for novel, bio-based polymers
industry
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the authors focus on the metabolic intermediate 2-pyrone-4,6-dicarboxylic acid as a potential raw material for novel, bio-based polymers
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Maruyama, K.
Interaction of 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase with Reactive Blue 2 and related dyes
J. Biochem.
103
714-721
1988
Pseudomonas straminea
brenda
Maruyama, K.
Isolation and identification of the reaction product of alpha-hydroxy-gamma-carboxymuconic epsilon-semialdehyde dehydrogenase
J. Biochem.
86
1671-1677
1979
Pseudomonas straminea
brenda
Maruyama, K.; Ariga, N.; Tsuda, M.; Deguchi, K.
Purification and properties of alpha-hydroxy-gamma-carboxymuconic epsilon-semialdehyde dehydrogenase
J. Biochem.
83
1125-1134
1978
Pseudomonas straminea
brenda
Masai, E.; Momose, K.; Hara, H.; Nisihikawa, S.; Katayama, Y.; Fukuda, M.
Genetic and biochemical characterization of 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase and its role in the protocatechuate 4,5-cleavage pathway in Sphingomonas paucimobilis SYK-6
J. Bacteriol.
182
6651-6658
2000
Sphingomonas paucimobilis, Sphingomonas paucimobilis SYK6
brenda
Maruyama, K.; Shibayama, T.; Ichikawa, A.; Sakou, Y.; Yamada, S.; Sugisaki, H.
Cloning and characterization of the genes encoding enzymes for the protocatechuate meta-degradation pathway of Pseudomonas ochraceae NGJ1
Biosci. Biotechnol. Biochem.
68
1434-1441
2004
Pseudomonas straminea, Pseudomonas straminea NGJ1
brenda
Otsuka, Y.; Nakamura, M.; Shigehara, K.; Sugimura, K.; Masai, E.; Ohara, S.; Katayama, Y.
Efficient production of 2-pyrone 4,6-dicarboxylic acid as a novel polymer-based material from protocatechuate by microbial function
Appl. Microbiol. Biotechnol.
71
608-614
2006
Sphingomonas paucimobilis, Sphingomonas paucimobilis SYK-6
brenda
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