Ligand ubiquinone-8

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Basic Ligand Information

Molecular Structure

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Molecular Formula

BRENDA Name

InChIKey

C₄₉H₇₄O₄

ubiquinone-8

ICFIZJQGJAJRSU-SGHXUWJISA-N

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Roles as Enzyme Ligand

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

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EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.2.5.1

pyruvate + ubiquinone-8 + H2O = acetate + CO2 + ubiquinol-8

702186, 700962

1.2.5.1

pyruvate + ubiquinone-8 = acetate + CO2 + ubiquinol-8

702194, 702185

1.2.5.1

2 entries

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

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EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

7.1.1.3

ubiquinol-8 + O2 + H+[side 1] = ubiquinone-8 + H2O + H+[side 2]

Substrate in Enzyme-catalyzed Reactions (6 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.2.5.1

pyruvate + ubiquinone-8 + H2O = acetate + CO2 + ubiquinol-8

702186, 704373, 700962

1.2.5.1

pyruvate + ubiquinone-8 = acetate + CO2 + ubiquinol-8

succinate + ubiquinone-8 = fumarate + ubiquinol-8

654820

1.8.5.9

[DsbA protein] with reduced L-cysteine residues + ubiquinone-8 = [DsbA protein] carrying a disulfide bond + ubiquinol-8

757516

7.1.1.2

NADH + ubiquinone-8 = NAD+ + ubiquinol-8

672041

7.2.1.1

NADH + H+ + ubiquinone-8 + n Na+/in = NAD+ + ubiquinol-8 + n Na+/out

725402

Product in Enzyme-catalyzed Reactions (3 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.10.3.11

2 ubiquinol-8 + O2 = 2 ubiquinone-8 + 2 H2O

7.1.1.3

ubiquinol-8 + O2 + H+/in = ubiquinone-8 + H2O + H+/out

7.1.1.3

ubiquinol-8 + O2 + H+[side 1] = ubiquinone-8 + H2O + H+[side 2]

7.1.1.3

2 entries

Enzyme Cofactor/Cosubstrate (7 results)

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EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.3.5.2

efficient, N-terminally truncated protein

656088

1.4.5.1

0.2 mM quinone stimulates reaction with D-alanine and oxidized 2,6-dichloroindophenol 2fold

394971

7.1.1.3

the bound ubiquinone at the QH site of cytochrome bo is essential for the catalytic turnover of the oxidase reactions, but it is not necessary for re-reduction of ferric heme b after the heme b-to-heme o electron transfer under flow-flash conditions

715003

7.1.1.3

the enzyme contains one equivalent of ubiquinone-8

714308

7.2.1.1

711269, 712407, 710746, 712274

7.2.1.1

complex contains one non-covalently bound FAD, one noncovalently bound riboflavin, ubiquinone-8 and a [2Fe–2S] cluster

731327

7.2.1.1

the enzyme contains one ubiquinone-8

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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EC NUMBER

ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

References & Links

Literature References (19)

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BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

394971

6102989

Purification and properties of D-amino acid dehydrogenase, an inducible membrane-bound iron-sulfur flavoenzyme from Escherichia coli B

1980

Olsiewski, P.J.; Kaczorowski, G.J.; Walsh, C.

J. Biol. Chem.

255

4487-4494

654820

11803023

Succinate dehydrogenase and fumrate reductase from Escherichia coli

2002

Cecchini, G.; Schröder, I.; GUnsalus, R.P.; Maklashina, E.

Biochim. Biophys. Acta

1553

140-157

656088

12189151

Malarial dihydroorotate dehydrogenase. Substrate and inhibitor specificity

2002

Baldwin, J.; Farajallah, A.M.; Malmquist, N.A.; Rathod, P.K.; Phillips, M.A.

J. Biol. Chem.

277

41827-41834

672041

15938640

Activation of isolated NADH:ubiquinone reductase I (complex I) from Escherichia coli by detergent and phospholipids. Recovery of ubiquinone reductase activity and changes in EPR signals of iron-sulfur clusters

2005

Sinegina, L.; Wikstroem, M.; Verkhovsky, M.I.; Verkhovskaya, M.L.

Biochemistry

8500-8506

700962

18988747

Structural basis for membrane binding and catalytic activation of the peripheral membrane enzyme pyruvate oxidase from Escherichia coli

2008

Neumann, P.; Weidner, A.; Pech, A.; Stubbs, M.T.; Tittmann, K.

Proc. Natl. Acad. Sci. USA

105

17390-17395

702185

6367818

Reconstitution of the membrane-bound, ubiquinone-dependent pyruvate oxidase respiratory chain of Escherichia coli with the cytochrome d terminal oxidase

1984

Koland, J.G.; Miller, M.J.; Gennis, R.B.

Biochemistry

445-453

702186

3527254

In vivo function of Escherichia coli pyruvate oxidase specifically requires a functional lipid binding site

1986

Grabau, C.; Cronan, J.E., Jr.

Biochemistry

3748-3751

702194

9305946

Sulfhydryl chemistry detects three conformations of the lipid binding region of Escherichia coli pyruvate oxidase

1997

Chang, Y.Y.; Cronan, J.E., Jr.

Biochemistry

11564-11573

704373

3897227

Reconstitution of the Ubiquinone-dependent pyruvate oxidase system of Escherichia coli with the cytochrome o terminal oxidase complex

1985

Carter, K.; Gennis, R.B.

J. Biol. Chem.

260

10986-10990

710746

21139223

Crystallization of the Na+-translocating NADH:quinone oxidoreductase from Vibrio cholerae

2010

Casutt, M.S.; Wendelspiess, S.; Steuber, J.; Fritz, G.

Acta Crystallogr. Sect. F

1677-1679

711269

15807651

Na+-translocating NADH:quinone oxidoreductase: progress achieved and prospects of investigations

2005

Bogachev, A.V.; Verkhovsky, M.I.

Biochemistry

143-149

711293

20056102

Sodium-translocating NADH:quinone oxidoreductase as a redox-driven ion pump

2010

Verkhovsky, M.I.; Bogachev, A.V.

Biochim. Biophys. Acta

1797

738-746

712274

17322313

Quinone reduction by the Na+-translocating NADH dehydrogenase promotes extracellular superoxide production in Vibrio cholerae

2007

Lin, P.C.; Turk, K.; Hase, C.C.; Fritz, G.; Steuber, J.

J. Bacteriol.

189

3902-3908

712407

19117949

Primary steps of the Na+-translocating NADH:ubiquinone oxidoreductase catalytic cycle resolved by the ultrafast freeze-quench approach

2009

Bogachev, A.V.; Belevich, N.P.; Bertsova, Y.V.; Verkhovsky, M.I.

J. Biol. Chem.

284

5533-5538

714308

20416270

The quinone-binding sites of the cytochrome bo3 ubiquinol oxidase from Escherichia coli

2010

Yap, L.L.; Lin, M.T.; Ouyang, H.; Samoilova, R.I.; Dikanov, S.A.; Gennis, R.B.

Biochim. Biophys. Acta

1797

1924-1932

715003

10471783

Role of a bound ubiquinone on reactions of the Escherichia coli cytochrome bo with ubiquinol and dioxygen

1999

Mogi, T.; Sato-Watanabe, M.; Miyoshi, H.; Orii, Y.

FEBS Lett.

457

223-226

725402

20558724

Localization and function of the membrane-bound riboflavin in the Na+-translocating NADH:quinone oxidoreductase (Na+-NQR) from Vibrio cholerae

2010

Casutt, M.S.; Huber, T.; Brunisholz, R.; Tao, M.; Fritz, G.; Steuber, J.

J. Biol. Chem.

285

27088-27099

731327

22366169

The single NqrB and NqrC subunits in the Na(+)-translocating NADH: quinone oxidoreductase (Na(+)-NQR) from Vibrio cholerae each carry one covalently attached FMN

2012

Casutt, M.S.; Schlosser, A.; Buckel, W.; Steuber, J.

Biochim. Biophys. Acta

1817

1817-1822

757516

18421137

Protein disulfide bond generation in Escherichia coli DsbB-DsbA

2008

Inaba, K.

J. Synchrotron Radiat.

199-201

Links to other databases for ubiquinone-8

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ChEBI

PubChem