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Ligand 8-oxo-GTP

Basic Ligand Information

Molecular Structure

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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

3.6.1.55

8-oxo-GTP + H2O = 8-oxo-GMP + diphosphate

716365

-

3.6.1.56

8-oxo-GTP + H2O = 8-oxo-GMP + diphosphate

716365

-

3.6.1.69

8-oxo-GTP + H2O = 8-oxo-GDP + phosphate

754103

-

Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Substrate (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.7.7.30

8-oxoguanosine triphosphate + L-fucose 1-phosphate = diphosphate + (8-oxoguanosine diphosphate)-L-fucose

661161

-

3.6.1.55

8-oxo-GTP + H2O = 8-oxo-GMP + diphosphate

667672, 756066, 716365

-

3.6.1.56

8-oxo-GTP + H2O = 8-oxo-GMP + diphosphate

716361, 716299, 716365

-

3.6.1.56

8-oxo-rGTP + H2O = 8-oxo-rGMP + diphosphate

758131

-

3.6.1.56

2 entries

3.6.1.69

8-oxo-GTP + H2O = 8-oxo-GDP + phosphate

754103, 752388

-

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.5.4.16

competitive inhibition, binds tightly to the enzyme with higher affinity than GTP, structure and binding network, overview

669149

-

3.5.4.16

competitive inhibitor

734606

-

3.5.4.16

competitive inhibitor. The inhibitor interacts with a conserved active site Cys149, and this residue is S-nitrosylated. Ki/Km: 0.022

756001

-

4.6.1.2

i.e. oxo8GTP, a potent competitive inhibitor of nitric oxide-stimulated soluble guanylyl cyclase

692446

-

4.6.1.2

i.e. oxo8GTP, a potent inhibitor of nitric oxide-stimulated soluble guanylyl cyclase

692446

-

3.5.4.16

3 entries

4.6.1.2

2 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.7.7.30

2.6

-

pH 7.0, 37°C

661161

3.6.1.56

2.6

-

pH 8.0, 30°C

716361

K_M Value (6 results)

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Show KM Value (6 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.7.7.30

0.0636

-

pH 7.0, 37°C

661161

3.5.4.25

0.21

-

-

246734

3.6.1.55

0.00026

-

pH 8.0, 30°C

667672

3.6.1.56

0.055

-

pH 8.0, 30°C

716361

3.6.1.56

0.082

-

at pH 7.4, temperature not specified in the publication

758131

3.6.1.56

0.29

-

pH 8.0, 30°C

716365

3.6.1.56

3 entries

K_i Value (2 results)

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Show KI Value (2 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.5.4.16

0.0000054

-

pH 8.5, 25°C, recombinant enzyme

669149

3.5.4.16

0.000149

-

pH and temperature not specified in the publication

756001

3.5.4.16

2 entries

IC₅₀ Value (2 results)

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Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

4.6.1.2

0.288

-

pH 7.4, 37°C, in presence of 0.05 mM GTP

692446

4.6.1.2

1.8

-

pH 7.4, 37°C, in presence of 0.5 mM GTP

692446

4.6.1.2

2 entries

References & Links

Literature References (14)

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Show Reference (14 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

246734

9756871

Potential of Escherichia coli GTP cyclohydrolase II for hydrolyzing 8-oxo-dGTP, a mutagenic substrate for DNA synthesis

1988

Kobayashi, M.; Ohara-Nemoto, Y.; Kaneko, M.; Hayakawa, H.; Sekiguchi, M.; Yamamoto, K.

J. Biol. Chem.

273

26394-26399

661161

16086588

Substrate discrimination by the human GTP fucose pyrophosphorylase

2005

Quirk, S.; Seley, K.L.

Biochemistry

44

10854-10863

667672

15850400

Multiple enzyme activities of Escherichia coli MutT protein for sanitization of DNA and RNA precursor pools

2005

Ito, R.; Hayakawa, H.; Sekiguchi, M.; Ishibashi, T.

Biochemistry

44

6670-6674

669149

16169877

Novel reaction mechanism of GTP cyclohydrolase I. High-resolution X-ray crystallography of Thermus thermophilus HB8 enzyme complexed with a transition state analogue, the 8-oxoguanine derivative

2005

Tanaka, Y.; Nakagawa, N.; Kuramitsu, S.; Yokoyama, S.; Masui, R.

J. Biochem.

138

263-275

692446

19167482

Characterization of oxidized guanosine 5-triphosphate as a viable inhibitor of soluble guanylyl cyclase

2009

Bolin, C.; Cardozo-Pelaez, F.

Free Radic. Biol. Med.

46

828-835

716299

20542142

Programmed cell death triggered by nucleotide pool damage and its prevention by MutT homolog-1 (MTH1) with oxidized purine nucleoside triphosphatase

2010

Nakabeppu, Y.; Oka, S.; Sheng, Z.; Tsuchimoto, D.; Sakumi, K.

Mutat. Res.

703

51-58

716361

11139615

Human MTH1 protein hydrolyzes the oxidized ribonucleotide, 2-hydroxy-ATP

2011

Fujikawa, K.; Kamiya, H.; Yakushiji, H.; Nakabeppu, Y.; Kasai, H.

Nucleic Acids Res.

29

449-454

716365

16002790

Mammalian enzymes for preventing transcriptional errors caused by oxidative damage

2005

Ishibashi, T.; Hayakawa, H.; Ito, R.; Miyazawa, M.; Yamagata, Y.; Sekiguchi, M.

Nucleic Acids Res.

33

3779-3784

734606

24745605

Biochemical and functional characterization of Plasmodium falciparum GTP cyclohydrolase I

2014

Kuempornsin, K.; Kotanan, N.; Chobson, P.; Kochakarn, T.; Jirawatcharadech, P.; Jaru-ampornpan, P.; Yuthavong, Y.; Chookajorn, T.

Malar. J.

13

150

752388

28375146

Biochemical and structural studies of Mycobacterium smegmatis MutT1, a sanitization enzyme with unusual modes of association

2017

Arif, S.; Patil, A.; Varshney, U.; Vijayan, M.

Acta Crystallogr. Sect. D

73

349-364

754103

23463507

Mycobacterium tuberculosis MutT1 (Rv2985) and ADPRase (Rv1700) proteins constitute a two-stage mechanism of 8-oxo-dGTP and 8-oxo-GTP detoxification and adenosine to cytidine mutation avoidance

2013

Patil, A.G.; Sang, P.B.; Govindan, A.; Varshney, U.

J. Biol. Chem.

288

11252-11262

756001

28126741

Mechanism and catalytic strategy of the prokaryotic-specific GTP cyclohydrolase-IB

2017

Paranagama, N.; Bonnett, S.A.; Alvarez, J.; Luthra, A.; Stec, B.; Gustafson, A.; Iwata-Reuyl, D.; Swairjo, M.A.

Biochem. J.

474

1017-1039

756066

30614695

Crystal structure and substrate specificity of the 8-oxo-dGTP hydrolase NUDT1 from Arabidopsis thaliana

2019

Jemth, A.S.; Scaletti, E.; Carter, M.; Helleday, T.; Stenmark, P.

Biochemistry

58

887-899

758131

26999531

MTH1 substrate recognition - an example of specific promiscuity

2016

Nissink, J.W.; Bista, M.; Breed, J.; Carter, N.; Embrey, K.; Read, J.; Winter-Holt, J.J.

PLoS ONE

11

e0151154

Links to other databases for 8-oxo-GTP

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Show Links (1 entry)

ChEBI

PubChem

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