dGTP (ECMDB01440) (M2MDB000389)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:52:48 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:11 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | dGTP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | dGTP is one of the two purine nucleotides that are used to synthesize DNA. It is an intermediate in purine metabolism pathway. It is a product of anaerobic ribonucleoside-triphosphate reductase (EC:1.17.4.2) and a substrate of deoxyguanosine triphosphate triphosphohydrolase (EC:3.1.5.1). (KEGG) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C10H16N5O13P3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 507.181 Monoisotopic: 506.995745159 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | HAAZLUGHYHWQIW-KVQBGUIXSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C10H16N5O13P3/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 2564-35-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | ({[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | dGTP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)N1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Purine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Purine deoxyribonucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Purine 2'-deoxyribonucleoside triphosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | 2 Flavodoxin reduced + Guanosine triphosphate + 2 Hydrogen ion > dGTP +2 flavodoxin semi oxidized + Water dGTP + Water > 2'-Deoxyguanosine 5'-monophosphate + Hydrogen ion + Pyrophosphate Adenosine triphosphate + dGDP <> ADP + dGTP dGTP + Water <> Deoxyguanosine + Triphosphate dGTP + DNA <> Pyrophosphate + DNA dGTP + Water <> 2'-Deoxyguanosine 5'-monophosphate + Pyrophosphate Adenosine triphosphate + dGDP <> ADP + dGTP dGTP + Pyruvic acid <> dGDP + Phosphoenolpyruvic acid dGTP + Uridine <> dGDP + Uridine 5'-monophosphate dGTP + Thioredoxin disulfide + Water <> Guanosine triphosphate + Thioredoxin dGTP + Cytidine <> dGDP + Cytidine monophosphate dGTP + hydroxyl radical > Hydrogen ion + 8-oxo-dGTP dGDP + Adenosine triphosphate > dGTP + ADP Water + dGTP > Hydrogen ion + Triphosphate + Deoxyguanosine dGTP + Water > Hydrogen ion + 2'-Deoxyguanosine 5'-monophosphate + Pyrophosphate dGTP + Water > Deoxyguanosine + Triphosphate dGDP + Adenosine triphosphate + dGDP > Adenosine diphosphate + dGTP + ADP Guanosine triphosphate + a reduced flavodoxin > dGTP + an oxidized flavodoxin + Water dGTP + Water <> Deoxyguanosine + Triphosphate dGTP + Thioredoxin disulfide + Water <> Guanosine triphosphate + Thioredoxin dGTP + DNA <> Pyrophosphate Adenosine triphosphate + dGDP <> ADP + dGTP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in nucleic acid binding
- Specific function:
- In addition to polymerase activity, this DNA polymerase exhibits 3' to 5' and 5' to 3' exonuclease activity. It is able to utilize nicked circular duplex DNA as a template and can unwind the parental DNA strand from its template
- Gene Name:
- polA
- Uniprot ID:
- P00582
- Molecular weight:
- 103117
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. The epsilon subunit contain the editing function and is a proofreading 3'-5' exonuclease
- Gene Name:
- dnaQ
- Uniprot ID:
- P03007
- Molecular weight:
- 27099
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in nucleotide binding
- Specific function:
- The gamma chain seems to interact with the delta subunit to transfer the beta subunit on the DNA
- Gene Name:
- dnaX
- Uniprot ID:
- P06710
- Molecular weight:
- 71137
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in nucleoside diphosphate kinase activity
- Specific function:
- Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate
- Gene Name:
- ndk
- Uniprot ID:
- P0A763
- Molecular weight:
- 15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate. |
- General function:
- Involved in ATP binding
- Specific function:
- ATP + uridine = ADP + UMP
- Gene Name:
- udk
- Uniprot ID:
- P0A8F4
- Molecular weight:
- 24353
Reactions
ATP + uridine = ADP + UMP. |
ATP + cytidine = ADP + CMP. |
- General function:
- Involved in DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The beta chain is required for initiation of replication once it is clamped onto DNA, it slides freely (bidirectional and ATP- independent) along duplex DNA
- Gene Name:
- dnaN
- Uniprot ID:
- P0A988
- Molecular weight:
- 40586
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in [formate-C-acetyltransferase]-activating enzyme activity
- Specific function:
- Activation of anaerobic ribonucleoside-triphosphate reductase under anaerobic conditions by generation of an organic free radical, using S-adenosylmethionine and reduced flavodoxin as cosubstrates to produce 5'-deoxy-adenosine
- Gene Name:
- nrdG
- Uniprot ID:
- P0A9N8
- Molecular weight:
- 17446
- General function:
- Involved in DNA binding
- Specific function:
- The exact function of the theta subunit is unknown
- Gene Name:
- holE
- Uniprot ID:
- P0ABS8
- Molecular weight:
- 8846
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in magnesium ion binding
- Specific function:
- ATP + pyruvate = ADP + phosphoenolpyruvate
- Gene Name:
- pykF
- Uniprot ID:
- P0AD61
- Molecular weight:
- 50729
Reactions
ATP + pyruvate = ADP + phosphoenolpyruvate. |
- General function:
- Involved in nucleoside-triphosphate diphosphatase activity
- Specific function:
- Specific function unknown
- Gene Name:
- mazG
- Uniprot ID:
- P0AEY3
- Molecular weight:
- 30412
Reactions
ATP + H(2)O = AMP + diphosphate. |
- General function:
- Involved in 3'-5' exonuclease activity
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The alpha chain is the DNA polymerase
- Gene Name:
- dnaE
- Uniprot ID:
- P10443
- Molecular weight:
- 129903
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in magnesium ion binding
- Specific function:
- dGTPase preferentially hydrolyzes dGTP over the other canonical NTPs
- Gene Name:
- dgt
- Uniprot ID:
- P15723
- Molecular weight:
- 59382
Reactions
dGTP + H(2)O = deoxyguanosine + triphosphate. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- ATP + pyruvate = ADP + phosphoenolpyruvate
- Gene Name:
- pykA
- Uniprot ID:
- P21599
- Molecular weight:
- 51357
Reactions
ATP + pyruvate = ADP + phosphoenolpyruvate. |
- General function:
- Involved in DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The delta subunit seems to interact with the gamma subunit to transfer the beta subunit on the DNA
- Gene Name:
- holA
- Uniprot ID:
- P28630
- Molecular weight:
- 38703
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity
- Gene Name:
- holB
- Uniprot ID:
- P28631
- Molecular weight:
- 36936
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in DNA-directed DNA polymerase activity
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The exact function of the psi subunit is unknown
- Gene Name:
- holD
- Uniprot ID:
- P28632
- Molecular weight:
- 15174
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Transports electrons between flavodoxin or ferredoxin and NADPH. Involved in the reductive activation of cobalamin- independent methionine synthase, pyruvate formate lyase and anaerobic ribonucleotide reductase. Also protects against superoxide radicals due to methyl viologen in the presence of oxygen
- Gene Name:
- fpr
- Uniprot ID:
- P28861
- Molecular weight:
- 27751
Reactions
2 reduced ferredoxin + NADP(+) + H(+) = 2 oxidized ferredoxin + NADPH. |
- General function:
- Involved in catalytic activity
- Specific function:
- 2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin
- Gene Name:
- nrdD
- Uniprot ID:
- P28903
- Molecular weight:
- 80022
Reactions
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin. |
- General function:
- Involved in DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity
- Gene Name:
- holC
- Uniprot ID:
- P28905
- Molecular weight:
- 16633
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in hydrolase activity
- Specific function:
- Hydrolyzes O6 atom-containing purine bases deoxyinosine triphosphate (dITP) and xanthosine triphosphate (XTP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) to nucleotide monophosphate and pyrophosphate. Probably excludes non- standard purines from DNA precursor pool, preventing thus incorporation into DNA and avoiding chromosomal lesions
- Gene Name:
- rdgB
- Uniprot ID:
- P52061
- Molecular weight:
- 21039
Reactions
A nucleoside triphosphate + H(2)O = a nucleotide + diphosphate. |
- General function:
- Involved in ATP binding
- Specific function:
- Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in the energy metabolism and nucleotide synthesis, is essential for maintenance and cell growth
- Gene Name:
- adk
- Uniprot ID:
- P69441
- Molecular weight:
- 23586
Reactions
ATP + AMP = 2 ADP. |
- General function:
- Involved in FMN binding
- Specific function:
- Low-potential electron donor to a number of redox enzymes (Potential)
- Gene Name:
- fldB
- Uniprot ID:
- P0ABY4
- Molecular weight:
- 19700
- General function:
- Involved in FMN binding
- Specific function:
- Low-potential electron donor to a number of redox enzymes (Potential). Involved in the reactivation of inactive cob(II)alamin in methionine synthase
- Gene Name:
- fldA
- Uniprot ID:
- P61949
- Molecular weight:
- 19737
- General function:
- Replication, recombination and repair
- Specific function:
- Involved in the GO system responsible for removing an oxidatively damaged form of guanine (7,8-dihydro-8-oxoguanine) from DNA and the nucleotide pool. 8-oxo-dGTP is inserted opposite dA and dC residues of template DNA with almost equal efficiency thus leading to A.T to G.C transversions. MutT specifically degrades 8-oxo-dGTP to the monophosphate
- Gene Name:
- mutT
- Uniprot ID:
- P08337
- Molecular weight:
- 14927
Reactions
8-oxo-dGTP + H(2)O = 8-oxo-dGMP + diphosphate. |
Transporters
- General function:
- Involved in nucleoside diphosphate kinase activity
- Specific function:
- Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate
- Gene Name:
- ndk
- Uniprot ID:
- P0A763
- Molecular weight:
- 15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate. |