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Ligand 2-oxo-2H-pyran-4,6-dicarboxylate

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

gallate degradation

KEGG

Aminobenzoate degradation, Benzoate degradation, Microbial metabolism in diverse environments

MetaCyc

3,4-dichlorobenzoate degradation, 3-chlorobenzoate degradation II (via protocatechuate), gallate degradation II, methylgallate degradation, protocatechuate degradation I (meta-cleavage pathway), syringate degradation more

Show all BRENDA pathways known for 2-oxo-2H-pyran-4,6-dicarboxylate

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.57

2-pyrone-4,6-dicarboxylate + H2O = 4-carboxy-2-hydroxyhexa-2,4-dienedioate

643840

-

3.1.1.57

2-pyrone-4,6-dicarboxylate + H2O = 4-oxalomesaconate

655061

-

3.1.1.57

2-pyrone-4,6-dicarboxylate + H2O = ?

710947

-

3.1.1.57

3 entries

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.312

4-carboxy-2-hydroxymuconate semialdehyde hemiacetal + NADP+ = 2-oxo-2H-pyran-4,6-dicarboxylate + NADPH + H+

0

-

1.13.11.8

gallic acid + O2 = 2-pyrone-4,6-dicarboxylic acid + H2O

0

-

Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Substrate (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.57

2-oxo-2H-pyran-4,6-dicarboxylate + H2O = (1E)-4-oxobut-1-ene-1,2,4-tricarboxylate

751355

-

3.1.1.57

2-pyrone-4,6-dicarboxylate + H2O = 4-carboxy-2-hydroxyhexa-2,4-dienedioate

643840

-

3.1.1.57

2-pyrone-4,6-dicarboxylate + H2O = 4-oxalomesaconate

655061, 718926

-

3.1.1.57

2-pyrone-4,6-dicarboxylate + H2O = ?

710947

-

3.1.1.57

4 entries

Product in Enzyme-catalyzed Reactions (5 results)

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Show Product (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.312

4-carboxy-2-hydroxymuconate semialdehyde hemiacetal + NADP+ = 2-oxo-2H-pyran-4,6-dicarboxylate + NADPH + H+

0

-

1.1.1.312

4-carboxy-2-hydroxymuconate semialdehyde + NADP+ = 2-pyrone-4,6-dicarboxylic acid + NADPH + H2O

0

-

1.1.1.312

protocatechuate + NADP+ + H2O = 2-pyrone-4,6-dicarboxylic acid + NADPH + H+

0

-

1.13.11.8

3-O-methylgallate + O2 = 4-carboxy-2-hydroxy-6-methoxy-6-oxohexa-2,4-dienoate + 2-pyrone-4,6-dicarboxylate

0

-

1.13.11.8

gallic acid + O2 = 2-pyrone-4,6-dicarboxylic acid + H2O

0

-

1.1.1.312

3 entries

1.13.11.8

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.312

non-competitive inhibition with respect to 4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde

288241

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (13 results)

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Show Turnover Number (13 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.1.1.57

0.0013

-

D248A mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.02

-

R124M mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.023

-

D248N mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.4

-

H31N mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.42

-

R217M mutant protein, pH 8.25, 30°C

718926

3.1.1.57

3.6

-

H33N mutant protein, pH 8.25, 30°C

718926

3.1.1.57

5

-

R130M mutant protein, pH 8.25, 30°C

718926

3.1.1.57

8

-

H180A mutant protein, pH 8.25, 30°C

718926

3.1.1.57

8.7

-

Y156F mutant protein, pH 8.25, 30°C

718926

3.1.1.57

26

-

Y49F mutant protein, pH 8.25, 30°C

718926

3.1.1.57

32

-

H180C mutant protein, pH 8.25, 30°C

718926

3.1.1.57

196

-

R183M mutant protein, pH 8.25, 30°C

718926

3.1.1.57

342

-

wild type protein, pH 8.25, 30°C

718926

3.1.1.57

13 entries

K_M Value (15 results)

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Show KM Value (15 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.1.1.57

0.041

-

H180C mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.048

-

wild type protein, pH 8.25, 30°C

718926

3.1.1.57

0.064

-

R183M mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.066

-

D248N mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.067

-

R217M mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.087

-

pH 8.5, 24°C

643840

3.1.1.57

0.089

-

H33N mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.09

-

R124M mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.094

-

pH 8.5, 25°C

655061

3.1.1.57

0.116

-

D248A mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.214

-

H180A mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.217

-

Y49F mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.238

-

Y156F mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.465

-

R130M mutant protein, pH 8.25, 30°C

718926

3.1.1.57

0.72

-

H31N mutant protein, pH 8.25, 30°C

718926

3.1.1.57

15 entries

References & Links

Literature References (6)

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Show Reference (6 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

288241

3170510

Interaction of 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase with Reactive Blue 2 and related dyes

1988

Maruyama, K.

J. Biochem.

103

714-721

643840

6841353

Purification and properties of 2-pyrone-4,6-dicarboxylate hydrolase

1983

Maruyama, K.

J. Biochem.

93

557-565

655061

15277747

Cloning and characterization of the genes encoding enzymes for the protocatechuate meta-degradation pathway of Pseudomonas ochraceae NGJ1

2004

Maruyama, K.; Shibayama, T.; Ichikawa, A.; Sakou, Y.; Yamada, S.; Sugisaki, H.

Biosci. Biotechnol. Biochem.

68

1434-1441

710947

20952641

Characterization of the protocatechuate 4,5-cleavage pathway operon in Comamonas sp. strain E6 and discovery of a novel pathway gene

2010

Kamimura, N.; Aoyama, T.; Yoshida, R.; Takahashi, K.; Kasai, D.; Abe, T.; Mase, K.; Katayama, Y.; Fukuda, M.; Masai, E.

Appl. Environ. Microbiol.

76

8093-8101

718926

22475079

Structure and catalytic mechanism of LigI: Insight into the amidohydrolase enzymes of cog3618 and lignin degradation

2012

Hobbs, M.E.; Malashkevich, V.; Williams, H.J.; Xu, C.; Sauder, J.M.; Burley, S.K.; Almo, S.C.; Raushel, F.M.

Biochemistry

51

3497-3507

751355

26188792

Theoretical study of the hydrolysis mechanism of 2-pyrone-4,6-dicarboxylate (PDC) catalyzed by LigI

2015

Zhang, S.; Ma, G.; Liu, Y.; Ling, B.

J. Mol. Graph. Model.

61

21-29

Links to other databases for 2-oxo-2H-pyran-4,6-dicarboxylate

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Show Links (1 entry)

ChEBI

PubChem