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Ligand cyclohexa-1,5-diene-1-carbonyl-CoA

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for cyclohexa-1,5-diene-1-carbonyl-CoA

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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

4.2.1.100

cyclohexa-1,5-diene-1-carbonyl-CoA + H2O = 6-hydroxycyclohex-1-ene-1-carbonyl-CoA

729651

-

4.2.1.100

cyclohexa-1,5-diene-1-carbonyl-CoA + H2O = 6-hydroxycyclohex-1-enecarbonyl-CoA

207952, 285201, 680480

-

4.2.1.100

cyclohexa-1,5-diene-1-carbonyl-CoA + H2O = 6-hydroxycyclohexa-1-ene-1-carbonyl-CoA

747850

-

4.2.1.100

3 entries

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

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Show Natural Product (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.7.8

benzoyl-CoA + reduced acceptor + ATP + H2O = cyclohexa-1,5-diene-1-carbonyl-CoA + acceptor + ADP + phosphate

0

-

1.3.7.8

benzoyl-CoA + reduced ferredoxin + 2 ATP + 2 H2O = cyclohexa-1,5-diene-1-carbonyl-CoA + oxidized ferredoxin + 2 ADP + 2 phosphate

0

-

1.3.7.8

benzoyl-CoA + reduced ferredoxin + ATP + H2O = cyclohexa-1,5-diene-1-carboxyl-CoA + oxidized ferredoxin + ADP + phosphate

0

-

1.3.7.8

3 entries

4.2.1.100

6-hydroxycyclohexa-1-ene-1-carbonyl-CoA = cyclohexa-1,5-diene-1-carbonyl-CoA + H2O

0

-

Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Substrate (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.8.10

cyclohex-1,5-diene-1-carbonyl-CoA + ferricenium hexafluorophosphate = benzoyl-CoA + ferrocenium hexafluorophosphate

742783

-

1.3.8.10

cyclohex-1,5-diene-1-carbonyl-CoA + Ti(III) citrate = cyclohex-1-ene-1-carbonyl-CoA + oxidized Ti(III) citrate

725285

-

1.3.8.10

cyclohexa-1,5-diene-1-carbonyl-CoA + ferricenium hexafluorophosphate = benzoyl-CoA + ferrocenium hexafluorophosphate

725285

-

4.2.1.100

cyclohexa-1,5-diene-1-carbonyl-CoA + H2O = 6-hydroxycyclohex-1-ene-1-carbonyl-CoA

207952, 285201, 747850, 729651

-

4.2.1.100

cyclohexa-1,5-diene-1-carbonyl-CoA + H2O = 6-hydroxycyclohex-1-enecarbonyl-CoA

207952, 285201, 680480

-

4.2.1.100

cyclohexa-1,5-diene-1-carbonyl-CoA + H2O = 6-hydroxycyclohexa-1-ene-1-carbonyl-CoA

747850

-

4.2.1.100

cyclohexa-1,5-dienecarbonyl-CoA + H2O = 6-hydroxycyclohex-1-ene-1-carbonyl-CoA

692753

-

1.3.8.10

3 entries

4.2.1.100

4 entries

Product in Enzyme-catalyzed Reactions (9 results)

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Show Product (9 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.7.8

benzoyl-CoA + reduced acceptor + ATP + H2O = cyclohexa-1,5-diene-1-carbonyl-CoA + acceptor + ADP + phosphate

0

-

1.3.7.8

benzoyl-CoA + reduced acceptor + ATP = cyclohexa-1,5-diene-1-carbonyl-CoA + acceptor + ADP + phosphate

12557, 12562, 12558, 12559

-

1.3.7.8

benzoyl-CoA + reduced ferredoxin + 2 ATP + 2 H2O = cyclohexa-1,5-diene-1-carbonyl-CoA + oxidized ferredoxin + 2 ADP + 2 phosphate

0

-

1.3.7.8

benzoyl-CoA + reduced ferredoxin + ATP = cyclohexa-1,5-diene-1-carbonyl-CoA + ferredoxin + ADP + phosphate

0

-

1.3.7.8

benzoyl-CoA + reduced methyl viologen + ATP = cyclohexa-1,5-diene-1-carbonyl-CoA + methyl viologen + ADP + phosphate

0

-

1.3.7.8

benzoyl-CoA + reduced ferredoxin + ATP + H2O = cyclohexa-1,5-diene-1-carboxyl-CoA + oxidized ferredoxin + ADP + phosphate

0

-

1.3.7.8

6 entries

1.3.8.10

cyclohex-1-ene-1-carbonyl-CoA + ferricenium hexafluorophosphate = cyclohex-1,5-diene-1-carbonyl-CoA + ferrocenium hexafluorophosphate

0

-

4.2.1.100

6-hydroxycyclohexa-1-ene-1-carbonyl-CoA = cyclohexa-1,5-diene-1-carbonyl-CoA + H2O

0

-

6.2.1.25

ATP + cyclohexa-1,5-diene-1-carboxylate + CoA = AMP + diphosphate + cyclohexa-1,5-diene-1-carboxyl-CoA

651721

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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Show Turnover Number (3 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

4.2.1.100

51

-

-

285201

4.2.1.100

175

-

pH 7.5, 30°C

680480

4.2.1.100

280

-

pH 7.5, 30°C

680480

4.2.1.100

3 entries

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

1.3.8.10

0.019

-

at pH 7.0 and 30°C

725285

1.3.8.10

0.085

-

pH 6.8, 30°C

742783

4.2.1.100

0.03

-

pH 7.5, 30°C

680480

4.2.1.100

0.085

-

pH 7.5, 30°C

680480

4.2.1.100

60

-

-

285201

1.3.8.10

2 entries

4.2.1.100

3 entries

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

12557

9490071

Identification, and characterization of the natural electron donor ferredoxin and of FAD as a possible prosthetic group of benzoyl-CoA reductase (dearomatizing), a key enzyme of anaerobic aromatic metabolism

1998

Boll , M.; Fuchs, G.

Eur. J. Biochem.

251

946-954

12558

9108255

Benzoyl-CoA reductase (dearomatizing), a key enzyme of anaerobic aromatic metabolism. A study of adenosinetriphosphatase activity, ATP stoichiometry of the reaction and EPR properties of the enzyme

1997

Boll, M.; Albracht, S.S.P.; Fuchs, G.

Eur. J. Biochem.

244

840-851

12559

8575453

Benzoyl-coenzyme A reductase (dearomatizing), a key enzyme of anaerobic aromatic metabolism. ATP dependence of the reaction, purification and some properties of the enzyme from Thaurea aromatica strain K172

1995

Boll, M.; Fuchs, G.

Eur. J. Biochem.

234

921-933

12562

9746358

Genes coding the benzoyl-CoA pathway of anaerobic metabolism in the bacterium Thauera aromatica

1998

Breese, K.; Boll, M.; Alt-Morbe, J.; Schagger, H.; Fuchs, G.

Eur. J. Biochem.

256

148-154

207952

8436125

Products of enzymatic reduction of benzoyl-CoA, a key reaction in anaerobic aromatic metabolism

1993

Koch, J.; Eisenreich, W.; Bacher, A.; Fuchs, G.

Eur. J. Biochem.

211

649-661

285201

9738901

Cyclohexa-1,5-diene-1-carboxyl-CoA hydratase, an enzyme involved in anaerobic metabolism of benzoyl-CoA in the denitrifying bacterium Thauera aromatica

1998

Lampe, D.; Eisenreich, W.; Bacher, A.; Fuchs, G.

Eur. J. Biochem.

255

618-627

651721

12897012

Benzoate-coenzyme A ligase from Thauera aromatica: an enzyme acting in anaerobic and aerobic pathways

2003

Schuhle, K.; Gescher, J.; Feil, U.; Paul, M.; Jahn, M.; Schagger, H.; Fuchs, G.

J. Bacteriol.

185

4920-4929

680480

17122342

Cyclohexa-1,5-diene-1-carbonyl-coenzyme A (CoA) hydratases of Geobacter metallireducens and Syntrophus aciditrophicus: Evidence for a common benzoyl-CoA degradation pathway in facultative and strict anaerobes

2007

Peters, F.; Shinoda, Y.; McInerney, M.J.; Boll, M.

J. Bacteriol.

189

1055-1060

692753

18826310

Mechanism of enzymatic Birch reduction: stereochemical course and exchange reactions of benzoyl-CoA reductase

2008

Thiele, B.; Rieder, O.; Golding, B.T.; Mueller, M.; Boll, M.

J. Am. Chem. Soc.

130

14050-14051

725285

23667239

Cyclohexanecarboxyl-coenzyme a (CoA) and cyclohex-1-ene-1-carboxyl-CoA dehydrogenases, two enzymes involved in the fermentation of benzoate and crotonate in Syntrophus aciditrophicus

2013

Kung, J.; Seifert, J.; von Bergen, M.; Bolla, M.

J. Bacteriol.

195

3193-3200

729651

25630364

Enzymes of the benzoyl-coenzyme A degradation pathway in the hyperthermophilic archaeon Ferroglobus placidus

2015

Schmid, G.; Rene, S.B.; Boll, M.

Environ. Microbiol.

17

3289-3300

742783

25112478

Enzymes involved in a novel anaerobic cyclohexane carboxylic acid degradation pathway

2014

Kung, J.W.; Meier, A.K.; Mergelsberg, M.; Boll, M.

J. Bacteriol.

196

3667-3674

747850

29312255

Promiscuous defluorinating enoyl-CoA hydratases/hydrolases allow for complete anaerobic degradation of 2-fluorobenzoate

2017

Tiedt, O.; Mergelsberg, M.; Eisenreich, W.; Boll, M.

Front. Microbiol.

8

2579

Links to other databases for cyclohexa-1,5-diene-1-carbonyl-CoA

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Show Links (1 entry)

ChEBI

PubChem