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Ligand 2-hydroxy-2,4-pentadienoate

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

KEGG

Benzoate degradation, Degradation of aromatic compounds, Dioxin degradation, Ethylbenzene degradation, Microbial metabolism in diverse environments, Phenylalanine metabolism, Styrene degradation, Xylene degradation more

MetaCyc

carbazole degradation, fluorene degradation I

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Roles as Enzyme Ligand

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

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.80

2-hydroxypent-2,4-dienoate = 2-keto-4-hydroxypentanoate

661714

-

5.3.2.6

2-hydroxy-2,4-pentadienoate = 2-oxopent-3-enoic acid

718847

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.7.1.14

(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O = (2E)-2-hydroxypenta-2,4-dienoate + succinate

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3.7.1.8

2-hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate + H2O = 2-hydroxypenta-2,4-dienoate + benzoate

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3.7.1.8

2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O = 2-hydroxypenta-2,4-dienoic acid + benzoate

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-

3.7.1.8

2 entries

Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.80

2-hydroxypent-2,4-dienoate + H2O = 2-keto-4-hydroxypentanoate

661714

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4.2.1.80

2-hydroxypent-2,4-dienoate = 2-keto-4-hydroxypentanoate

661714

-

4.2.1.80

2-hydroxypentadienoic acid = ?

648401

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5.3.2.6

2-hydroxy-2,4-pentadienoate = (3E)-2-oxopent-3-enoate

726964

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5.3.2.6

2-hydroxy-2,4-pentadienoate = 2-oxo-4-pentenoate

721792

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5.3.2.6

2-hydroxy-2,4-pentadienoate = 2-oxopent-3-enoic acid

718847

-

4.2.1.80

3 entries

5.3.2.6

3 entries

Product in Enzyme-catalyzed Reactions (18 results)

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Show Product (18 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.7.1.13

2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoate + H2O = anthranilate + 2-hydroxypenta-2,4-dienoate

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3.7.1.13

2-hydroxy-6-oxo-6-(2'-aminophenyl)hexa-2,4-dienoic acid + H2O = benzoic acid + 2-hydroxypenta-2,4-dienoic acid

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3.7.1.13

2 entries

3.7.1.14

(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O = (2E)-2-hydroxypenta-2,4-dienoate + succinate

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3.7.1.25

2-hydroxy-6-oxo-6-(2'-aminophenyl)hexa-2,4-dienoate + H2O = 2-hydroxypenta-2,4-dienoate + benzoate

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3.7.1.8

(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid + H2O = 4-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid

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3.7.1.8

(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O = benzoate + (2E)-2-hydroxypenta-2,4-dienoic acid

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3.7.1.8

(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O = 2-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid

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3.7.1.8

(2E,4E)-6-(3,4-dichlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O = 3,4-dichlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid

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3.7.1.8

(2E,4E)-6-(3,5-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O = 3,5-dichlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid

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3.7.1.8

(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O = 3-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid

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3.7.1.8

2,6-dihydroxy-6-phenylhexa-2,4-dienoate = benzaldehyde + (2E)-2-hydroxypenta-2,4-dienoic acid

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3.7.1.8

2-hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate + H2O = 2-hydroxypenta-2,4-dienoate + benzoate

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3.7.1.8

2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O = benzoate + 2-hydroxypenta-2,4-dienoate

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3.7.1.8

2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoic acid + H2O = 2-aminobenzoic acid + 2-hydroxypenta-2,4-dienoic acid

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3.7.1.8

2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O = 2-hydroxypenta-2,4-dienoic acid + benzoate

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3.7.1.8

2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O = benzoate + 2-hydroxypenta-2,4-dienoic acid

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3.7.1.8

8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid + H2O = 2-hydroxypenta-2,4-dienoic acid + benzoate

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3.7.1.8

13 entries

5.3.2.6

2-oxopent-4-enoate = 2-hydroxy-2,4-pentadienoate

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Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (6 results)

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Show Turnover Number (6 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

4.2.1.80

215

-

activated by Mn2+

661714

4.2.1.80

361

-

activated by Mg2+

661714

5.3.2.6

0.1

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pH 7.3, 23°C

721792

5.3.2.6

0.4

-

pH 7.3, 23°C, wild-type enzyme

718830

5.3.2.6

1

-

pH 7.3, 23°C, mutant R11A

718830

5.3.2.6

2.5

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pH 7.3, 23°C

721792

4.2.1.80

2 entries

5.3.2.6

4 entries

K_M Value (7 results)

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Show KM Value (7 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

4.2.1.80

0.0317

-

activated by Mg2+

661714

4.2.1.80

0.0386

-

activated by Mn2+

661714

4.2.1.80

0.041

-

pH 6

648401

5.3.2.6

0.09

-

pH 7.3, 23°C

721792

5.3.2.6

0.19

-

pH 7.3, 23°C

721792

5.3.2.6

1.11

-

pH 7.3, 23°C, mutant R11A

718830

5.3.2.6

1.11

-

pH 7.3, 23°C, wild-type enzyme

718830

4.2.1.80

3 entries

5.3.2.6

4 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

648401

9492273

Purification, characterization and reaction mechanism of monofunctional 2-hydroxypentadienoic acid hydratase from Escherichia coli

1998

Pollard, J.R.; Bugg, T.D.H.

Eur. J. Biochem.

251

98-106

661714

15691330

Determination of the metal ion dependence and substrate specificity of a hydratase involved in the degradation pathway of biphenyl/chlorobiphenyl

2005

Wang, P.; Seah, S.Y.K.

FEBS J.

272

966-974

718830

10493802

Kinetic, stereochemical, and structural effects of mutations of the active site arginine residues in 4-oxalocrotonate tautomerase

1999

Harris, T.K.; Czerwinski, R.M.; Johnson, W.H.; Legler, P.M.; Abeygunawardana, C.; Massiah, M.A.; Stivers, J.T.; Whitman, C.P.; Mildvan, A.S.

Biochemistry

38

12343-12357

718847

17902707

Kinetic and stereochemical analysis of YwhB, a 4-oxalocrotonate tautomerase homologue in Bacillus subtilis: Mechanistic implications for the YwhB- and 4-oxalocrotonate tautomerase-catalyzed reactions

2007

Wang, S.; Johnson Jr., W.; Czerwinski, R.; Stamps, S.; Whitman, C.

Biochemistry

46

11919-11929

721792

20709352

Kinetic and structural characterization of DmpI from Helicobacter pylori and Archaeoglobus fulgidus, two 4-oxalocrotonate tautomerase family members

2010

Almrud, J.J.; Dasgupta, R.; Czerwinski, R.M.; Kern, A.D.; Hackert, M.L.; Whitman, C.P.

Bioorg. Chem.

38

252-259

726964

21809870

Kinetic, crystallographic, and mechanistic characterization of TomN: elucidation of a function for a 4-oxalocrotonate tautomerase homologue in the tomaymycin biosynthetic pathway

2011

Burks, E.A.; Yan, W.; Johnson, W.H.; Li, W.; Schroeder, G.K.; Min, C.; Gerratana, B.; Zhang, Y.; Whitman, C.P.

Biochemistry

50

7600-7611

Links to other databases for 2-hydroxy-2,4-pentadienoate

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Show Links (1 entry)

ChEBI

PubChem

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