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Ligand citraconic acid

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for citraconic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.35

2-Methylmaleate + H2O = ?

5672, 5673

-

Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Substrate (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.31

2-methylmaleic acid + NAD(P)H = (R)-2-methylsuccinic acid + NAD(P)+

689312

-

1.3.1.31

citraconate + NADH + H+ = 2-methylsuccinic acid + NAD+

763423

-

1.3.1.31

citraconate + NADPH + H+ = 2-methylsuccinic acid + NADP+

763423

-

1.3.1.42

(2Z)-2-methylbut-2-enedioic acid + NADH = (2R)-2-methylbutanedioic acid + NAD+

684429

-

1.3.1.42

(2Z)-2-methylbut-2-enedioic acid + NADPH = (2R)-2-methylbutanedioic acid + NADP+

684429

-

1.3.1.31

3 entries

1.3.1.42

2 entries

1.3.1.6

citraconic acid + NADH = 2-methylbutanedioic acid + NAD+

390838

-

4.2.1.31

citraconate = D-citramalate

5648, 5645, 5647

-

4.2.1.33

citraconate = ?

5663, 5664

-

4.2.1.35

2-Methylmaleate + H2O = (R)-2-Methylmalate

2493, 5672, 5673, 5671

-

4.2.1.35

2-Methylmaleate + H2O = ?

5672, 5673

-

4.2.1.35

2 entries

Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.7.1.23

6-methylmaleylpyruvate + H2O = 2-methylmaleate + pyruvate

0

-

5.3.3.6

itaconate = methylmaleate

0

-

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.6

-

390838

-

1.3.1.6

preincubation

390838

-

1.3.1.6

slight inhibition

390836

-

1.3.1.6

3 entries

4.2.1.2

-

33771

-

5.5.1.5

-

3718

-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

2.5.1.72

5kts, 3D-view

Enzyme Kinetic Parameters

K_M Value (5 results)

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Show KM Value (5 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

4.2.1.31

0.2

-

-

5647

4.2.1.31

4.55

-

-

5648

4.2.1.33

0.083

-

crude enzyme preparation

5663

4.2.1.33

1.79

-

crude enzyme preparation

5664

4.2.1.31

2 entries

4.2.1.33

2 entries

4.2.1.35

1.1

-

-

5671

References & Links

Literature References (16)

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Show Reference (16 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2493

-

The molecular cloning of genes specifying some enzymes of the 3,5-xylenol degradative pathway

1996

Jain, R.K.

Appl. Microbiol. Biotechnol.

45

502-508

3718

240704

Metabolism of aromatic compounds by fungi. Kinetic properties and mechanism of 3-carboxy-cis,cis-muconate cyclase from Aspergillus niger

1975

Thatcher, D.R.; Cain, R.B.

Eur. J. Biochem.

56

193-204

5645

-

Effect of maleate counterion on malease activity: production of D-malate in a crystal-liquid two-phase system

1995

Van der Werf, M.J.; Hartmans, S.; Van der Tweel, W.J.J.

Enzyme Microb. Technol.

17

430-436

5647

16349034

Purification and characterization of maleate hydratase from Pseudomonas pseudoalcaligenes

1993

Van der Werf, M.J.; Van der Tweel, W.J.J.; Hartmans, S.

Appl. Environ. Microbiol.

59

2823-2829

5648

-

The substrate specificity of maleate hydratase from Arthrobacter sp. strain MCI2612

1994

Ueda, M.; Yamada, H.; Asano, Y.

Appl. Microbiol. Biotechnol.

41

215-218

5663

3071717

Isopropylmalate dehydratase from yeast

1988

Kohlhaw, G.B.

Methods Enzymol.

166

423-429

5664

-

Some properties of the leucine-biosynthesizing enzymes from Candida maltosa

1991

Bode, R.; Birnbaum, D.

J. Basic Microbiol.

31

21-26

5671

4296839

Purification and properties of citraconase

1968

Subramanian, S.S.; Raghavendra Rao, M.R.

J. Biol. Chem.

243

2367-2372

5672

6989805

Regulation of enzymes of the 3,5-xylenol-degradative pathway in Pseudomonas putida: evidence for a plasmid

1980

Hopper, D.J.; Kemp, P.D.

J. Bacteriol.

142

21-26

5673

-

Characterization and physical analysis of a 3,5-xylenol degradative plasmid in Pseudomonas putida

1984

Jain, R.K.; Bayly, R.C.; Skurray, R.A.

J. Gen. Microbiol.

130

3019-3028

33771

8203917

Initial kinetic and mechanistic characterization of Escherichia coli fumarase A

1994

Flint, D.H.

Arch. Biochem. Biophys.

311

509-516

390836

4960892

Fumarate reductase activity of Streptococcus faecalis

1967

Aue, B.J.; Deibel, R.H.

J. Bacteriol.

93

1770-1776

390838

44997

Properties and function of fumarate reductase (NADH) in Streptococcus lactis

1979

Hillier, A.J.; Jericho, R.E.; Green, S.M.; Jago, G.R.

Aust. J. Biol. Sci.

32

625-635

684429

17431865

Asymmetric bioreduction of activated alkenes using cloned 12-oxophytodienoate reductase isoenzymes OPR-1 and OPR-3 from Lycopersicon esculentum (tomato): a striking change of stereoselectivity

2007

Hall, M.; Stueckler, C.; Kroutil, W.; Macheroux, P.; Faber, K.

Angew. Chem.

46

3934-3937

689312

18031047

Stereocomplementary bioreduction of alpha,beta-unsaturated dicarboxylic acids and dimethyl esters using enoate reductases: enzyme- and substrate-based stereocontrol

2007

Stueckler, C.; Hall, M.; Ehammer, H.; Pointner, E.; Kroutil, W.; Macheroux, P.; Faber, K.

Org. Lett.

9

5409-5411

763423

29155059

Microbial production of branched-chain dicarboxylate 2-methylsuccinic acid via enoate reductase-mediated bioreduction

2018

Wang, J.; Yang, Y.; Zhang, R.; Shen, X.; Chen, Z.; Wang, J.; Yuan, Q.; Yan, Y.

Metab. Eng.

45

1-10

Links to other databases for citraconic acid

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Show Links (1 entry)

ChEBI

PubChem