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MetaCyc Compound: dTTP

Systematic Name: thymidine 5'-(tetrahydrogen triphosphate)

Synonyms: thymidine triphosphate, thymidine 5'-triphosphate, TTP

Superclasses: a nucleic acid componenta nucleotidea 2'-deoxyribonucleotidea deoxyribonucleoside triphosphatea pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid componenta nucleotidea 2'-deoxyribonucleotidea pyrimidine 2'-deoxyribonucleotidea pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid componenta nucleotidea nucleoside triphosphatea deoxyribonucleoside triphosphatea pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid componenta nucleotidea pyrimidine nucleotidea pyrimidine 2'-deoxyribonucleotidea pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda diazinea pyrimidinea pyrimidine nucleotidea pyrimidine 2'-deoxyribonucleotidea pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda diazinea pyrimidine

Chemical Formula: C10H13N2O14P3

Molecular Weight: 478.14 Daltons

Monoisotopic Molecular Weight: 481.9892627955 Daltons

dTTP compound structure

SMILES: CC1(=CN(C(=O)NC(=O)1)C2(CC(O)C(COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])O2))

InChI: InChI=1S/C10H17N2O14P3/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(24-8)4-23-28(19,20)26-29(21,22)25-27(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,21,22)(H,11,14,15)(H2,16,17,18)/p-4/t6-,7+,8+/m0/s1

InChIKey: InChIKey=NHVNXKFIZYSCEB-XLPZGREQSA-J

Unification Links: CAS:365-08-2, ChEBI:37568, ChemSpider:10160750, HMDB:HMDB01342, IAF1260:35032, KEGG:C00459, MetaboLights:MTBLC37568, PubChem:11988283

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -559.63837Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
dTTP + H2O → dTDP + phosphate + H+
dTTP + 2 H2O → dTMP + 2 phosphate + 2 H+
dTTP + H2O → dTMP + diphosphate + H+

phytol salvage pathway :
phytyl monophosphate + a nucleoside triphosphate → phytyl diphosphate + a nucleoside diphosphate

pyrimidine deoxyribonucleosides salvage :
2'-deoxycytidine + a nucleoside triphosphate → dCMP + a nucleoside diphosphate + H+

Not in pathways:
a nucleoside triphosphate + H2O → a nucleoside diphosphate + phosphate + H+
a nucleoside triphosphate + H2O → a nucleoside 5'-monophosphate + diphosphate + H+
a nucleoside triphosphate + 2 H2O → a nucleoside 5'-monophosphate + 2 phosphate + 2 H+

Not in pathways:
a nucleotide + H2O → a nucleoside + phosphate

Reactions known to produce the compound:

pyrimidine deoxyribonucleotide phosphorylation , pyrimidine deoxyribonucleotides biosynthesis from CTP , pyrimidine deoxyribonucleotides de novo biosynthesis I , pyrimidine deoxyribonucleotides de novo biosynthesis II , pyrimidine deoxyribonucleotides de novo biosynthesis III , pyrimidine deoxyribonucleotides de novo biosynthesis IV , superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis (E. coli) :
dTDP + ATP → dTTP + ADP

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

Reactions known to both consume and produce the compound:

dTDP-3-acetamido-3,6-dideoxy-α-D-glucose biosynthesis , dTDP-3-acetamido-α-D-fucos biosynthesis , dTDP-4-O-demethyl-β-L-noviose biosynthesis , dTDP-6-deoxy-α-D-allose biosynthesis , dTDP-α-D-mycaminose biosynthesis , dTDP-β-L-4-epi-vancosamine biosynthesis , dTDP-β-L-digitoxose biosynthesis , dTDP-D-β-fucofuranose biosynthesis , dTDP-D-desosamine biosynthesis , dTDP-D-forosamine biosynthesis , dTDP-D-olivose, dTDP-D-oliose and dTDP-D-mycarose biosynthesis , dTDP-D-ravidosamine and dTDP-4-acetyl-D-ravidosamine biosynthesis , dTDP-L-megosamine biosynthesis , dTDP-L-mycarose biosynthesis , dTDP-L-olivose biosynthesis , dTDP-L-rhamnose biosynthesis I , dTDP-L-rhamnose biosynthesis II , dTDP-N-acetylthomosamine biosynthesis , dTDP-N-acetylviosamine biosynthesis :
α-D-glucopyranose 1-phosphate + dTTP + H+ ↔ dTDP-α-D-glucose + diphosphate

In Reactions of unknown directionality:

Not in pathways:
α-D-galactose 1-phosphate + dTTP + H+ = dTDP-α-D-galactose + diphosphate

Not in pathways:
a deoxyribonucleoside triphosphate + an oxidized thioredoxin + H2O = a ribonucleoside triphosphate + a reduced thioredoxin
a deoxyribonucleoside triphosphate + (deoxynucleotides)(n) = (deoxynucleotides)(n+1) + diphosphate
a deoxyribonucleoside triphosphate + (deoxynucleotides)(n) = (deoxynucleotides)(n+1) + diphosphate
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 + AMP = a nucleoside diphosphate + ADP
a nucleoside triphosphate + RNA(n) = RNA(n+1) + diphosphate
RNA(n) + a nucleoside triphosphate = RNA(n+1) + diphosphate
a nucleoside triphosphate + an α-D-aldose 1-phosphate + H+ = a nucleoside diphosphate-hexose + diphosphate
a gentamicin + a nucleoside triphosphate = a 2-nucleotidylgentamicin + diphosphate

Not in pathways:
a nucleotide + a 2'-deoxynucleoside = a nucleoside + a 2'-deoxyribonucleoside 5'-monophosphate

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

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

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

Inhibitor (Competitive) of: GTP cyclohydrolase [Yim76], thymidine kinase [Okazaki64, Chen78, Iwatsuki67, Comment 2], dTDP-glucose 4,6-dehydratase [Vara88], cytidine 5'-monophosphate N-acetylneuraminate synthetase [RodriguezAparic92] Inhibitor (Allosteric) of: dCMP deaminase [Hou08], deoxycytidylate deaminase [McIntosh86], deoxycytidylate deaminase [Weiner93] Inhibitor (Mechanism unknown) of: dTMP kinase [Nelson69, Helmward89, Comment 3], dCTP deaminase [Johansson07], dihydroneopterin triphosphate pyrophosphohydrolase [Suzuki74], deoxyribonucleoside 5'-monophosphate phosphatase [Proudfoot04], ribonucleoside-triphosphate reductase [Eliasson94, Comment 4], dCTP deaminase [Li03b], dTDP-L-dihydrostreptose:streatidine-6-phosphate dihydrostreptosyltransferase [Kniep80], UDP-glucuronate decarboxylase [Pattathil05], UDP-glucuronate decarboxylase [Harper02]

This compound has been characterized as an alternative substrate of the following enzymes: 2'-deoxyadenosine kinase, dTMP kinase (GTP), UMP kinase, 2'-deoxyguanosine kinase, dCMP kinase, dGMP kinase (GTP), [protein-PII] uridylyltransferase, acetate kinase, 5,10-methenyltetrahydrofolate synthetase, 8-oxo-7,8-dihydro-deoxyguanosine-triphosphate pyrophosphohydrolase, NAD kinase, alkaline phosphatase, D-tagatose-6-phosphate kinase


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

Harper02: Harper AD, Bar-Peled M (2002). "Biosynthesis of UDP-xylose. Cloning and characterization of a novel Arabidopsis gene family, UXS, encoding soluble and putative membrane-bound UDP-glucuronic acid decarboxylase isoforms." Plant Physiol 130(4);2188-98. PMID: 12481102

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

Hou08: Hou HF, Liang YH, Li LF, Su XD, Dong YH (2008). "Crystal structures of Streptococcus mutans 2'-deoxycytidylate deaminase and its complex with substrate analog and allosteric regulator dCTP x Mg2+." J Mol Biol 377(1);220-31. PMID: 18255096

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

Johansson07: Johansson E, Thymark M, Bynck JH, Fano M, Larsen S, Willemoes M (2007). "Regulation of dCTP deaminase from Escherichia coli by nonallosteric dTTP binding to an inactive form of the enzyme." FEBS J 274(16);4188-98. PMID: 17651436

Kniep80: Kniep B, Grisebach H (1980). "Biosynthesis of streptomycin. Purification and properties of a dTDP-L-dihydrostreptose: streptidine-6-phosphate dihydrostreptosyltransferase from Streptomyces griseus." Eur J Biochem 105(1);139-44. PMID: 6768553

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Li03b: Li H, Xu H, Graham DE, White RH (2003). "The Methanococcus jannaschii dCTP deaminase is a bifunctional deaminase and diphosphatase." J Biol Chem 278(13);11100-6. PMID: 12538648

McIntosh86: McIntosh EM, Haynes RH (1986). "Sequence and expression of the dCMP deaminase gene (DCD1) of Saccharomyces cerevisiae." Mol Cell Biol 6(5);1711-21. PMID: 3023902

Nelson69: Nelson DJ, Carter CE (1969). "Purification and characterization of Thymidine 5-monophosphate kinase from Escherichia coli B." J Biol Chem 1969;244(19);5254-62. PMID: 4899016

Okazaki64: Okazaki R, Kornberg A (1964). "Deoxythymidine Kinase of Escherichia coli I. Purification and some properties of the enzyme." J Biol Chem 1964;239(1):269-274.

Okazaki64a: Okazaki R, Kornberg A "Deoxythymidine Kinase of Escherichia coli II. Kinetics and feedback control." J Biol Chem 1964;239(1):275-284.

Pattathil05: Pattathil S, Harper AD, Bar-Peled M (2005). "Biosynthesis of UDP-xylose: characterization of membrane-bound AtUxs2." Planta 221(4);538-48. PMID: 15655675

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

RodriguezAparic92: Rodriguez-Aparicio LB, Luengo JM, Gonzalez-Clemente C, Reglero A (1992). "Purification and characterization of the nuclear cytidine 5'-monophosphate N-acetylneuraminic acid synthetase from rat liver." J Biol Chem 267(13);9257-63. PMID: 1577759

Suzuki74: Suzuki Y, Brown GM (1974). "The biosynthesis of folic acid. XII. Purification and properties of dihydroneopterin triphosphate pyrophosphohydrolase." J Biol Chem 1974;249(8);2405-10. PMID: 4362677

Vara88: Vara JA, Hutchinson CR (1988). "Purification of thymidine-diphospho-D-glucose 4,6-dehydratase from an erythromycin-producing strain of Saccharopolyspora erythraea by high resolution liquid chromatography." J Biol Chem 263(29);14992-5. PMID: 3170573

Weiner93: Weiner KX, Weiner RS, Maley F, Maley GF (1993). "Primary structure of human deoxycytidylate deaminase and overexpression of its functional protein in Escherichia coli." J Biol Chem 268(17);12983-9. PMID: 7685356

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 MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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