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Escherichia coli K-12 substr. MG1655 Compound: dGTP

Synonyms: 2'-deoxyguanosine-5'-triphosphate, deoxy-GTP, deoxyguanosine-triphosphate

Superclasses: a nucleic acid component
a nucleic acid componenta nucleotidea 2'-deoxyribonucleotidea deoxyribonucleoside triphosphatea purine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid componenta nucleotidea 2'-deoxyribonucleotidea purine 2'-deoxyribonucleotidea purine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid componenta nucleotidea nucleoside triphosphatea deoxyribonucleoside triphosphatea purine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid componenta nucleotidea purine nucleotidea purine 2'-deoxyribonucleotidea purine 2'-deoxyribonucleoside 5'-triphosphate
an organic heterocyclic compoundan organic heterobicyclic compounda purinea purine nucleotidea purine 2'-deoxyribonucleotidea purine 2'-deoxyribonucleoside 5'-triphosphate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda purinea purine nucleotidea purine 2'-deoxyribonucleotidea purine 2'-deoxyribonucleoside 5'-triphosphate


Chemical Formula: C10H12N5O13P3

Molecular Weight: 503.15 Daltons

Monoisotopic Molecular Weight: 506.99574515689994 Daltons

dGTP compound structure

SMILES: C(OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])C1(OC(CC(O)1)N3(C=NC2(C(=O)NC(N)=NC=23)))

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)/p-4/t4-,5+,6+/m0/s1

InChIKey: InChIKey=HAAZLUGHYHWQIW-KVQBGUIXSA-J

Unification Links: CAS:2564-35-4, ChEBI:61429, HMDB:HMDB01440, IAF1260:34502, KEGG:C00286, PubChem:25246112

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -631.739

Reactions known to consume the compound:

Not in pathways:
dGTP + 2 hydroxyl radical → 8-oxo-dGTP + H2O
dGTP + H2O → dGMP + diphosphate + H+
dGTP + H2O → PPPi + 2'-deoxyguanosine + H+

Not in pathways:
a nucleoside triphosphate + H2O → a nucleoside 5'-monophosphate + diphosphate + H+

Reactions known to produce the compound:

guanosine deoxyribonucleotides de novo biosynthesis II :
dGDP + ATP → dGTP + ADP
dGTP + an oxidized flavodoxin + H2O ← GTP + a reduced flavodoxin

Not in pathways:
a nucleoside diphosphate + ATP → a nucleoside triphosphate + ADP

In Reactions of unknown directionality:

Not in pathways:
a deoxyribonucleoside triphosphate + (deoxynucleotides)(n) = (deoxynucleotides)(n+1) + diphosphate
a reduced flavodoxin + a ribonucleoside triphosphate = an oxidized flavodoxin + a deoxyribonucleoside triphosphate + H2O

Not in pathways:
a nucleoside triphosphate + RNA(n) = RNA(n+1) + diphosphate

Enzymes activated by dGTP, sorted by the type of activation, are:

Activator (Allosteric) of: ribonucleoside-triphosphate reductase [Eliasson94, Comment 1], thymidine kinase [Iwatsuki67, Chen78]

Enzymes inhibited by dGTP, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: GTP cyclohydrolase [Yim76], guanylate kinase [Oeschger66, Comment 2] Inhibitor (Mechanism unknown) of: deoxyribonucleoside 5'-monophosphate phosphatase [Proudfoot04], ribonucleoside-triphosphate reductase [Eliasson94, Comment 3]

This compound has been characterized as an alternative substrate of the following enzymes: thymidine kinase, alkaline phosphatase, alkaline phosphatase, xanthosine triphosphate pyrophosphatase


References

Chen78: Chen MS, Prusoff WH (1978). "Thymidine kinase from Escherichia coli." Methods Enzymol 1978;51;354-60. PMID: 357898

Eliasson94: Eliasson R, Pontis E, Sun X, Reichard P (1994). "Allosteric control of the substrate specificity of the anaerobic ribonucleotide reductase from Escherichia coli." J Biol Chem 269(42);26052-7. PMID: 7929317

Iwatsuki67: Iwatsuki N, Okazaki R (1967). "Mechanism of regulation of deoxythymidine kinase of Escherichia coli. I. Effect of regulatory deoxynucleotides on the state of aggregation of the enzyme." J Mol Biol 1967;29(1);139-54. PMID: 4861610

Oeschger66: Oeschger MP, Bessman MJ (1966). "Purification and properties of guanylate kinase from Escherichia coli." J Biol Chem 1966;241(22);5452-60. PMID: 5333666

Proudfoot04: Proudfoot M, Kuznetsova E, Brown G, Rao NN, Kitagawa M, Mori H, Savchenko A, Yakunin AF (2004). "General enzymatic screens identify three new nucleotidases in Escherichia coli. Biochemical characterization of SurE, YfbR, and YjjG." J Biol Chem 279(52);54687-94. PMID: 15489502

Yim76: Yim JJ, Brown GM (1976). "Characteristics of guanosine triphosphate cyclohydrolase I purified from Escherichia coli." J Biol Chem 1976;251(16);5087-94. PMID: 821948


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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