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Escherichia coli K-12 substr. MG1655 Compound: dTTP

Systematic Name: thymidine 5'-(tetrahydrogen triphosphate)

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

Superclasses: a nucleic acid component a nucleotide a 2'-deoxyribonucleotide a deoxyribonucleoside triphosphate a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid component a nucleotide a 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid component a nucleotide a nucleoside triphosphate a deoxyribonucleoside triphosphate a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
a nucleic acid component a nucleotide a pyrimidine nucleotide a pyrimidine 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a diazine a pyrimidine a pyrimidine nucleotide a pyrimidine 2'-deoxyribonucleotide a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a diazine a pyrimidine

Chemical Formula: C10H13N2O14P3

Molecular Weight: 478.14 Daltons

Monoisotopic Molecular Weight: 481.9892627955 Daltons

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 Change Formation (ΔfG in kcal/mol): -688.17

Reactions known to consume the compound:

Not in pathways:
dTTP + H2O → dTMP + diphosphate + H+


a nucleoside triphosphate + H2O → a nucleoside 5'-monophosphate + diphosphate + H+

Reactions known to produce the compound:

pyrimidine deoxyribonucleotide phosphorylation , pyrimidine deoxyribonucleotides de novo biosynthesis I , pyrimidine deoxyribonucleotides de novo biosynthesis II , 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-L-rhamnose biosynthesis I , dTDP-N-acetylthomosamine biosynthesis :
α-D-glucose 1-phosphate + dTTP + H+ ↔ dTDP-α-D-glucose + diphosphate

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


a nucleoside triphosphate + RNA(n) = RNA(n+1) + diphosphate

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 [Okazaki64a, Chen78, Iwatsuki67, Comment 2]

Inhibitor (Mechanism unknown) of: deoxyribonucleoside 5'-monophosphate phosphatase [Proudfoot04] , dihydroneopterin triphosphate pyrophosphohydrolase [Suzuki74] , dCTP deaminase [Johansson07] , ribonucleoside-triphosphate reductase [Eliasson94, Comment 3] , dTMP kinase [Nelson69, Helmward89, Comment 4]


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

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

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

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

Okazaki64a: 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. PMID: 14114853

Okazaki64b: Okazaki R, Kornberg A "Deoxythymidine Kinase of Escherichia coli II. Kinetics and feedback control." J Biol Chem 1964;239(1):275-284.

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

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

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
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, biocyc14.