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Ligand trans-2-enoyl-CoA

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

KEGG

Fatty acid elongation

MetaCyc

fatty acid beta-oxidation I (generic), fatty acid beta-oxidation II (plant peroxisome), fatty acid beta-oxidation III (unsaturated, odd number), fatty acid beta-oxidation IV (unsaturated, even number), fatty acid beta-oxidation V (unsaturated, odd number, di-isomerase-dependent), fatty acid beta-oxidation VI (mammalian peroxisome), fatty acid beta-oxidation VII (yeast peroxisome), methyl ketone biosynthesis (engineered), polyhydroxydecanoate biosynthesis more

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Natural Substrate (5 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.3.1.38

740717

trans-2-enoyl-CoA + NADPH + H+ = acyl-CoA + NADP+

-

1.3.1.38

740376

trans-2,3-dehydroacyl-CoA + NADPH + H+ = acyl-CoA + NADP+

-

1.3.1.38

2 entries

1.3.1.44

656287

trans-didehydroacyl-CoA + NAD(P)H = acyl-CoA + NAD(P)+

-

4.2.1.119

685405, 687487, 747869, 746834, 749314, 747321, 665519, 659723

(2E)-2-enoyl-CoA + H2O = (3R)-3-hydroxyacyl-CoA

-

4.2.1.119

714098

(2E)-enoyl-CoA + H2O = (3R)-hydroxyacyl-CoA

-

4.2.1.119

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (7 results)

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Show Natural Product (7 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.3.3.6

, 391072

acyl-CoA + O2 = trans-2,3-dehydroacyl-CoA + H2O2

-

1.3.8.7

391360, 391325

acyl-CoA + electron transfer flavoprotein = 2,3-dehydroacyl-CoA + reduced electron transfer flavoprotein

-

4.2.1.119

-

(3R)-3-hydroxyacyl-CoA = (2E)-2-enoyl-CoA + H2O

-

4.2.1.134

-

3-hydroxyacyl-CoA = 2,3-trans-enoyl-CoA + H2O

-

4.2.1.17

-

(3S)-3-hydroxyacyl-CoA = (E)-2(or 3)-enoyl-CoA + H2O

-

5.3.3.8

-

a (3E)-alk-3-enoyl-CoA = a (2E)-alk-2-enoyl-CoA

-

5.3.3.8

-

a (3Z)-alk-3-enoyl-CoA = a (2E)-alk-2-enoyl-CoA

-

5.3.3.8

2 entries

Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.3.1.38

740717

trans-2-enoyl-CoA + NADPH + H+ = acyl-CoA + NADP+

-

1.3.1.38

740376

trans-2,3-dehydroacyl-CoA + NADPH + H+ = acyl-CoA + NADP+

-

1.3.1.38

2 entries

1.3.1.44

656287

trans-didehydroacyl-CoA + NAD(P)H = acyl-CoA + NAD(P)+

-

4.2.1.119

685405, 687487, 747869, 746834, 749314, 747321, 665519, 659723

(2E)-2-enoyl-CoA + H2O = (3R)-3-hydroxyacyl-CoA

-

4.2.1.119

714098, 684952

(2E)-enoyl-CoA + H2O = (3R)-hydroxyacyl-CoA

-

4.2.1.119

2 entries

4.2.1.17

684952, 704681

(2E)-enoyl-CoA + H2O = (3S)-hydroxyacyl-CoA

-

Product in Enzyme-catalyzed Reactions (12 results)

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Show Product (12 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.3.1.38

-

acyl-CoA + NADP+ = trans-2,3-dehydroacyl-CoA + NADPH

-

1.3.3.6

-

acyl-CoA + O2 = trans-2-enoyl-CoA + H2O2

-

1.3.3.6

391072, , 391071, 391043, 391069, 391070, 391066

acyl-CoA + O2 = trans-2,3-dehydroacyl-CoA + H2O2

-

1.3.8.7

391325, 391349, 391354, 391346, 391322, 391268, 391275, 391351, 391350, 391282, 391272, 391203, 391201,

acyl-CoA + acceptor = 2,3-dehydroacyl-CoA + reduced acceptor

-

1.3.8.7

391360, 391325

acyl-CoA + electron transfer flavoprotein = 2,3-dehydroacyl-CoA + reduced electron transfer flavoprotein

-

1.3.3.6

2 entries

1.3.8.7

2 entries

1.3.8.8

-

acyl-CoA + acceptor = 2,3-dehydroacyl-CoA + reduced acceptor

-

1.3.8.9

-

acyl-CoA + acceptor = 2,3-dehydroacyl-CoA + reduced acceptor

-

4.2.1.119

-

(3R)-3-hydroxyacyl-CoA = (2E)-2-enoyl-CoA + H2O

-

4.2.1.134

-

3-hydroxyacyl-CoA = 2,3-trans-enoyl-CoA + H2O

-

4.2.1.17

-

(3S)-3-hydroxyacyl-CoA = (E)-2(or 3)-enoyl-CoA + H2O

-

5.3.3.8

-

a (3E)-alk-3-enoyl-CoA = a (2E)-alk-2-enoyl-CoA

-

5.3.3.8

-

a (3Z)-alk-3-enoyl-CoA = a (2E)-alk-2-enoyl-CoA

-

5.3.3.8

2 entries

Enzyme Kinetic Parameters

References & Links

Literature References (34)

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Show Reference (34 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

391043

7400120

Purification and properties of acyl-CoA oxidase from rat liver

1980

Osumi, T.; Hashimoto, T.; Ui, N.

J. Biochem.

87

1735-1746

391066

11147819

Purification and characterization of the recombinant form of acyl CoA oxidase 3 from the yeast Yarrowia lipolytica

2000

Luo, Y.S.; Wang, H.J.; Gopalan, K.V.; Srivastava, D.K.; Nicaud, J.M.; Chardot, T.

Arch. Biochem. Biophys.

384

1-8

391069

8973574

Higher-plant medium- and short-chain acyl-CoA oxidases: identification, purification and characterization of two novel enzymes of eukaryotic peroxisomal.beta-oxidation

1996

Hooks, M.A.; Bode, K.; Couee, I.

Biochem. J.

320

607-614

391070

10571860

Long-chain acyl-CoA oxidases of Arabidopsis

1999

Hooks, M.A.; Kellas, F.; Graham, I.A.

Plant J.

20

1-13

391071

-

Estimation of peroxisomal.beta-oxidation in rat heart by a direct assay of acyl-CoA oxidase

1994

Chu, C.; Mao, L.F.; Schulz, H.

Biochem. J.

302

23-29

391072

10672038

cDNA cloning and analysis of tissue-specific expression of mouse peroxisomal straight-chain acyl-CoA oxidase

2000

Nohammer, C.; El-Shabrawi, Y.; Schauer, S.; Hiden, M.; Berger, J.; Forss-Petter, S.; Winter, E.; Eferl, R.; Zechner, R.; Hoefler, G.

Eur. J. Biochem.

267

1254-1260

391201

3597357

Purification and properties of short chain acyl-CoA, medium chain acyl-CoA, and isovaleryl-CoA dehydrogenases from human liver

1987

Finocchiaro, G.; Ito, M.; Tanaka, K.

J. Biol. Chem.

262

7982-7989

391203

6401712

Separation and properties of five distinct acyl-CoA dehydrogenases from rat liver mitochondria. Identification of a new 2-methyl branched chain acyl-CoA dehydrogenase

1983

Ikeda, Y.; Dabrowski, C.; Tanaka, K.

J. Biol. Chem.

258

1066-1076

391268

4084576

Spectroscopic analysis of the interaction of rat liver short-chain, medium-chain, and long-chain acyl coenzyme A dehydrogenases with acyl coenzyme A substrates

1985

Ikeda, Y.; Okamura-Ikeda, K.; Tanaka, K.

Biochemistry

24

7192-7199

391272

3968063

Purification and characterization of short-chain, medium-chain, and long-chain acyl-CoA dehydrogenases from rat liver mitochondria. Isolation of the holo- and apoenzymes and conversion of the apoenzyme to the holoenzyme

1985

Ikeda, Y.; Okamura-Ikeda, K.; Tanaka, K.

J. Biol. Chem.

260

1311-1325

391275

6546382

Purification and properties of acyl coenzyme A dehydrogenases from bovine liver. Formation of 2-trans,4-cis-decadienoyl coenzyme A

1984

Dommes, V.; Kunau, W.H.

J. Biol. Chem.

259

1789-1797

391282

7334008

Purification and properties of rat liver acyl-CoA dehydrogenases and electron transfer flavoprotein

1981

Furuta, S.; Miyazawa, S.; Hashimoto, T.

J. Biochem.

90

1739-1750

391322

3355170

The nature of enzyme-substrate complexes in acyl-coenzyme A dehydrogenases

1988

Lau, S.M.; Thorpe, C.

Arch. Biochem. Biophys.

262

293-297

391325

-

Fatty acid oxidation in cultured skin fibroblasts from patients with inherited disorders of fatty acid metabolism: studies on the specificity of acyl-CoA dehydrogenases

1987

Chalmers, R.A.; English, N.

Biochem. Soc. Trans.

15

489-491

391346

7074078

Reactions of beta-(2-furyl)propionyl coenzyme A with general fatty acyl-CoA dehydrogenase

1982

McFarland, J.T.; Lee, M.Y.; Reinsch, J.; Raven, W.

Biochemistry

21

1224-1229

391349

7317051

Inhibition of general acyl CoA dehydrogenase by electron transfer flavoprotein semiquinone

1981

Beckmann, J.D.; Frerman, F.E.; McKean, M.C.

Biochem. Biophys. Res. Commun.

102

1290-1294

391350

7278660

Acyl-CoA dehydrogenases from pig liver mitochondria

1981

Hall, C.L.

Methods Enzymol.

71

375-385

391351

7278659

Acyl-CoA dehydrogenase from pig kidney

1981

Thorpe, C.

Methods Enzymol.

71

366-374

391354

7440536

Enzyme-activated inhibitors, alternate substrates, and a dead end inhibitor of the general acyl-CoA dehydrogenase

1980

Frerman, F.E.; Miziorko, H.M.; Beckmann, J.D.

J. Biol. Chem.

255

11192-11198

391360

640208

Fatty acyl-coenzyme A dehydrogenases

1978

Engel, P.C.

Biochem. Soc. Trans.

6

76-80

656287

15569691

Mitochondrial trans-2-enoyl-CoA reductase of wax ester fermentation from Euglena gracilis defines a new family of enzymes involved in lipid synthesis

2005

Hoffmeister, M.; Piotrowski, M.; Nowitzki, U.; Martin, W.

J. Biol. Chem.

280

4329-4338

659723

15644212

Crystal structure of 2-enoyl-CoA hydratase 2 from human peroxisomal multifunctional enzyme type 2

2005

Kristian Koski, M.; Haapalainen, A.M.; Hiltunen, J.K.; Glumoff, T.

J. Mol. Biol.

345

1157-1169

665519

15051722

A two-domain structure of one subunit explains unique features of eukaryotic hydratase 2

2004

Koski, M.K.; Haapalainen, A.M.; Hiltunen, J.K.; Glumoff, T.

J. Biol. Chem.

279

24666-24672

684952

-

Recombinant 2-enoyl-CoA hydratase derived from rat peroxisomal multifunctional enzyme 2: role of the hydratase reaction in bile acid synthesis

1997

Qin, Y.; Haapalainen, A.M.; Conry, D.; Cuebas, D.A.; Hiltunen, J.K.; Novikov, D.K.

Biochem. J.

328

377-382

685405

8507679

Peroxisomal beta-oxidation of polyunsaturated fatty acids

1993

Hiltunen, J.K.; Filppula, S.A.; Haeyrinen, H.M.; Koivuranta, K.T.; Hakkola, E.H.

Biochimie

75

175-182

687487

1551874

Peroxisomal multifunctional beta-oxidation protein of Saccharomyces cerevisiae. Molecular analysis of the fox2 gene and gene product

1992

Hiltunen, J.K.; Wenzel, B.; Beyer, A.; Erdmann, R.; Fossa, A.; Kunau, W.H.

J. Biol. Chem.

267

6646-6653

704681

20463028

The crystal structure of liganded rat peroxisomal multifunctional enzyme type 1: a flexible molecule with two interconnected active sites

2010

Kasaragod, P.; Venkatesan, R.; Kiema, T.R.; Hiltunen, J.K.; Wierenga, R.K.

J. Biol. Chem.

285

24089-24098

714098

21320074

Peroxisomal multifunctional enzyme type 2 from the fruitfly: dehydrogenase and hydratase act as separate entities, as revealed by structure and kinetics

2011

Haataja, T.J.; Koski, M.K.; Hiltunen, J.K.; Glumoff, T.

Biochem. J.

435

771-781

740376

25031892

A novel cytosolic isoform of mitochondrial trans-2-enoyl-CoA reductase enhances peroxisome proliferator-activated receptor alpha activity

2014

Kim, D.G.; Yoo, J.C.; Kim, E.; Lee, Y.S.; Yarishkin, O.V.; Lee, D.Y.; Lee, K.H.; Hong, S.G.; Hwang, E.M.; Park, J.Y.

Endocrinol. Metab. (Seoul)

29

185-194

740717

24220030

Mutation for nonsyndromic mental retardation in the trans-2-enoyl-CoA reductase TER gene involved in fatty acid elongation impairs the enzyme activity and stability, leading to change in sphingolipid profile

2013

Abe, K.; Ohno, Y.; Sassa, T.; Taguchi, R.; Caliskan, M.; Ober, C.; Kihara, A.

J. Biol. Chem.

288

36741-36749

746834

26386053

Contribution of the distal pocket residue to the acyl-chain-length specificity of (R)-specific enoyl-coenzyme A hydratases from Pseudomonas spp.

2015

Tsuge, T.; Sato, S.; Hiroe, A.; Ishizuka, K.; Kanazawa, H.; Shiro, Y.; Hisano, T.

Appl. Environ. Microbiol.

81

8076-8083

747321

28532241

Bacillus cereus-type polyhydroxyalkanoate biosynthetic gene cluster contains R-specific enoyl-CoA hydratase gene

2017

Kihara, T.; Hiroe, A.; Ishii-Hyakutake, M.; Mizuno, K.; Tsuge, T.

Biosci. Biotechnol. Biochem.

81

1627-1635

747869

26925070

Suppressor screen and phenotype analyses revealed an emerging role of the monofunctional peroxisomal enoyl-CoA hydratase 2 in compensated cell enlargement

2016

Katano, M.; Takahashi, K.; Hirano, T.; Kazama, Y.; Abe, T.; Tsukaya, H.; Ferjani, A.

Front. Plant Sci.

7

132

749314

27052994

Enoyl-CoA hydratase mediates polyhydroxyalkanoate mobilization in Haloferax mediterranei

2016

Liu, G.; Cai, S.; Hou, J.; Zhao, D.; Han, J.; Zhou, J.; Xiang, H.

Sci. Rep.

6

24015

Links to other databases for trans-2-enoyl-CoA

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Show Links (1 entry)