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Ligand tetrafluoro-1,4-benzoquinone

Basic Ligand Information

Molecular Structure

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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

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.1.1.404

741332

2,3,5,6-tetrachloro-1,4-benzoquinone + NADH + H+ = 2,3,5,6-tetrachlorohydroquinone + NAD+

-

1.14.13.50

659022

tetrachlorobenzoquinone + NADPH = tetrachlorohydroquinone + NADP+

-

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

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Show Natural Product (3 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.1.1.404

-

2,3,5,6-tetrachlorohydroquinone + NAD+ = 2,3,5,6-tetrachloro-1,4-benzoquinone + NADH + H+

-

1.14.13.50

-

pentachlorophenol + NADPH + O2 = tetrachlorobenzoquinone + NADP+ + chloride + H2O

-

1.14.13.50

-

pentachlorophenol + NADPH + H+ + O2 = 2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O

-

1.14.13.50

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

1.1.1.404

741332

2,3,5,6-tetrachloro-1,4-benzoquinone + NADH + H+ = 2,3,5,6-tetrachlorohydroquinone + NAD+

-

1.1.3.10

724062

D-glucose + tetrafluoro-1,4-benzoquinone = ?

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1.1.3.10

389649, 699081

tetrafluoro-1,4-benzoquinone + O2 = ? + H2O2

-

1.1.99.29

686685

D-glucose + tetrafluoro-1,4-benzoquinone = ?

-

1.1.99.29

686685

D-glucose + tetrachloro-1,4-benzoquinone = ?

-

1.1.3.10

2 entries

1.1.99.29

2 entries

1.14.13.50

659022

tetrachlorobenzoquinone + NADPH = tetrachlorohydroquinone + NADP+

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Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.1.1.404

-

2,3,5,6-tetrachlorohydroquinone + NAD+ = 2,3,5,6-tetrachloro-1,4-benzoquinone + NADH + H+

-

1.1.1.404

-

2,3,5,6-tetrachlorohydroquinone + NADP+ = 2,3,5,6-tetrachloro-1,4-benzoquinone + NADPH + H+

-

1.1.1.404

2 entries

1.11.1.7

-

pentachlorophenol + H2O2 = 2,3,5,6-tetrachloro-1,4-benzoquinone + HCl

-

1.14.13.50

-

pentachlorophenol + 2 NADPH + H+ + O2 = tetrachlorobenzoquinone + 2 NADP+ + chloride + H2O

-

1.14.13.50

-

pentachlorophenol + NADPH + O2 = tetrachlorobenzoquinone + NADP+ + chloride + H2O

-

1.14.13.50

-

pentachlorophenol + NADH + H+ + O2 = 2,3,5,6-tetrachloro-1,4-benzoquinone + NAD+ + chloride + H2O

-

1.14.13.50

-

pentachlorophenol + NADPH + H+ + O2 = 2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O

-

1.14.13.50

4 entries

Inhibitor in Enzyme-catalyzed Reactions (6 results)

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Show Inhibitors (6 entries)

COMMENTARY

EC NUMBER

LITERATURE

ENZYME 3D STRUCTURE

inactivates the enzyme, feedback control

1.14.13.50

659022

-

strong inhibition of succinate-phenazine methosulfate-(1,4-dichloroindophenol) oxidoreductase

1.3.5.1

679618

-

i.e. TCBQ, inhibition of GSTA1-2 and GSTA1-1 by 70-80%, and GSTA2-2 by 25%, binds to cysteine residues of the enzyme, e.g. Cys17 of GSTA1-1, via a first reversible step to covalent binding, overview, Kitz-Wilson inactivation model

2.5.1.18

671916

-

-

2.7.1.33

722018

-

-

3.5.1.5

688019

-

-

3.5.1.88

687836

-

-

3 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

COMMENTARY

EC NUMBER

LITERATURE

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

pH 6.5, 30°C, recombinant enzyme

1.1.3.10

724062

129

-

substrate tetrafluoro-1,4-benzoquinone (constant D-glucose concentration, 20 mM), activity determined spectrophotometrically at 420 nm by measuring formation of H2O2 with a horse-radish peroxidase-coupled assay using 2,2'-azinobis(3-ethylbenzthiazolinesulfonic acid) as the chromogen, 30°C, pH 6.5

1.1.3.10

699081

6.61

-

K_M Value (6 results)

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Show KM Value (6 entries)

COMMENTARY

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

LITERATURE

pH 6.5, 30°C, recombinant enzyme

1.1.3.10

9.42

-

724062

pH 6.5, substrate: D-glucose

1.1.3.10

0.22

-

389649

pH 6.5, substrate: D-glucose

1.1.3.10

0.088

-

389649

pH 6.5, substrate: D-glucose

2 entries

substrate tetrafluoro-1,4-benzoquinone (constant D-glucose concentration, 20 mM), activity determined spectrophotometrically at 420 nm by measuring formation of H2O2 with a horse-radish peroxidase-coupled assay using 2,2'-azinobis(3-ethylbenzthiazolinesulfonic acid) as the chromogen, 30°C, pH 6.5

1.1.3.10

0.64

-

699081

at 30°C with 25 mM glucose as susbtrate

1.1.99.29

0.39

-

686685

at 30°C with 25 mM glucose as susbtrate

1.1.99.29

0.28

-

686685

at 30°C with 25 mM glucose as susbtrate

2 entries

K_i Value (1 result)

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Show KI Value (1 entry)

COMMENTARY

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

LITERATURE

-

3.5.1.5

0.00045

-

688019

IC₅₀ Value (2 results)

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Show IC50 Value (2 entries)

COMMENTARY

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

LITERATURE

isoform PanK3, at pH 7.5 and 37°C

2.7.1.33

0.0059

-

722018

fluorescence polarization assay

3.5.1.88

0.048

-

687836

References & Links

Literature References (11)

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Show Reference (11 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

389649

11472941

Purification and characterization of pyranose oxidase from the white rot fungus Trametes multicolor

2001

Leitner, C.; Volc, J.; Haltrich, D.

Appl. Environ. Microbiol.

67

3636-3644

659022

12486067

A previously unrecognized step in pentachlorophenol degradation in Sphingobium chlorophenolicum is catalyzed by tetrachlorobenzoquinone reductase (PcpD)

2003

Dai, M.; Rogers, J.B.; Warner, J.R.; Copley, S.D.

J. Bacteriol.

185

302-310

671916

16620786

Chemical modification at subunit 1 of rat kidney alpha class glutathione transferase with 2,3,5,6-tetrachloro-1,4-benzoquinone: close structural connectivity between glutathione conjugation activity and non-substrate ligand binding

2006

O'Sullivan, S.M.; McCarthy, R.M.; Vargo, M.A.; Colman, R.F.; Sheehan, D.

Biochem. Pharmacol.

71

1629-1636

679618

1935955

Purification and characterisation of an archaebacterial succinate dehydrogenase complex from the plasma membrane of the thermoacidophile Sulfolobus acidocaldarius.

1991

Moll, R.; Schäfer, G.

Eur. J. Biochem.

201

593-600

686685

17227387

Properties of pyranose dehydrogenase purified from the litter-degrading fungus Agaricus xanthoderma

2007

Kujawa, M.; Volc, J.; Halada, P.; Sedmera, P.; Divne, C.; Sygmund, C.; Leitner, C.; Peterbauer, C.; Haltrich, D.

FEBS J.

274

879-894

687836

17435169

High-throughput identification of inhibitors of human mitochondrial peptide deformylase

2007

Antczak, C.; Shum, D.; Escobar, S.; Bassit, B.; Kim, E.; Seshan, V.E.; Wu, N.; Yang, G.; Ouerfelli, O.; Li, Y.M.; Scheinberg, D.A.; Djaballah, H.

J. Biomol. Screen.

12

521-535

688019

17194024

Inhibition of jack bean urease by tetrachloro-o-benzoquinone and tetrachloro-p-benzoquinone

2006

Kot, M.; Zaborska, W.

J. Enzyme Inhib. Med. Chem.

21

537-542

699081

19501263

Pyranose 2-oxidase from Phanerochaete chrysosporium--expression in E. coli and biochemical characterization

2009

Pisanelli, I.; Kujawa, M.; Spadiut, O.; Kittl, R.; Halada, P.; Volc, J.; Mozuch, M.D.; Kersten, P.; Haltrich, D.; Peterbauer, C.

J. Biotechnol.

142

97-106

722018

20797618

Modulation of pantothenate kinase 3 activity by small molecules that interact with the substrate/allosteric regulatory domain

2010

Leonardi, R.; Zhang, Y.M.; Yun, M.K.; Zhou, R.; Zeng, F.Y.; Lin, W.; Cui, J.; Chen, T.; Rock, C.O.; White, S.W.; Jackowski, S.

Chem. Biol.

17

892-902

724062

21968652

Heterologous expression and biochemical characterization of novel pyranose 2-oxidases from the ascomycetes Aspergillus nidulans and Aspergillus oryzae

2012

Pisanelli, I.; Wuehrer, P.; Reyes-Dominguez, Y.; Spadiut, O.; Haltrich, D.; Peterbauer, C.

Appl. Microbiol. Biotechnol.

93

1157-1166

741332

23676275

Sequestration of a highly reactive intermediate in an evolving pathway for degradation of pentachlorophenol

2013

Yadid, I.; Rudolph, J.; Hlouchova, K.; Copley, S.D.

Proc. Natl. Acad. Sci. USA

110

E2182-E2190

Links to other databases for tetrafluoro-1,4-benzoquinone

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Show Links (1 entry)

ChEBI

PubChem

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