| Record Information |
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| Version | 2.0 |
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| Creation Date | 2012-05-31 13:50:21 -0600 |
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| Update Date | 2015-09-13 12:56:10 -0600 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | Thymidine 5'-triphosphate |
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| Description | Thymidine triphosphate or TTP is one of the four nucleoside triphosphates that make up DNA. It can be used by DNA ligase to create overlapping "sticky ends" so that protruding ends of opened microbial plasmids maybe closed up. |
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| Structure | |
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| Synonyms: | - 2'-Deoxythymidine 5'-triphosphate
- 2'-Deoxythymidine 5'-triphosphoric acid
- 2'-Deoxythymidine triphosphate
- 2'-Deoxythymidine triphosphoric acid
- 5'-TTP
- 5-Methyl-dUTP
- Deoxy-TTP
- Deoxythymidine 5'-triphosphate
- Deoxythymidine 5'-triphosphoric acid
- Deoxythymidine triphosphate
- Deoxythymidine triphosphoric acid
- DTTP
- Thymidine 5'-triphosphate
- Thymidine 5'-triphosphoric acid
- Thymidine mono(tetrahydrogen triphosphate)
- Thymidine mono(tetrahydrogen triphosphoric acid)
- Thymidine triphosphate
- Thymidine triphosphoric acid
- TTP
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| Chemical Formula: | C10H17N2O14P3 |
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| Weight: | Average: 482.1683
Monoisotopic: 481.989262798 |
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| InChI Key: | NHVNXKFIZYSCEB-XLPZGREQSA-N |
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| 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)/t6-,7+,8+/m0/s1 |
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| CAS number: | 365-08-2 |
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| IUPAC Name: | {[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid |
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| Traditional IUPAC Name: | dTTP |
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| SMILES: | CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. |
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| Kingdom | Organic compounds |
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| Super Class | Nucleosides, nucleotides, and analogues |
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| Class | Pyrimidine nucleotides |
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| Sub Class | Pyrimidine deoxyribonucleotides |
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| Direct Parent | Pyrimidine 2'-deoxyribonucleoside triphosphates |
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| Alternative Parents | |
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| Substituents | - Pyrimidine 2'-deoxyribonucleoside triphosphate
- Pyrimidone
- Monoalkyl phosphate
- Hydropyrimidine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Pyrimidine
- Alkyl phosphate
- Heteroaromatic compound
- Vinylogous amide
- Tetrahydrofuran
- Lactam
- Secondary alcohol
- Urea
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Alcohol
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State: | Solid |
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| Charge: | -3 |
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| Melting point: | Not Available |
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| Experimental Properties: | |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations: | Cytoplasm |
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| Reactions: | |
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| SMPDB Pathways: | | O-antigen building blocks biosynthesis | PW002089 |    | | Pyrimidine metabolism | PW000942 |    | | Secondary Metabolites: enterobacterial common antigen biosynthesis | PW000959 |    | | Secondary Metabolites: enterobacterial common antigen biosynthesis 2 | PW002045 |    | | Secondary Metabolites: enterobacterial common antigen biosynthesis 3 | PW002046 |    | | Starch and sucrose metabolism | PW000941 |    | | purine nucleotides de novo biosynthesis | PW000910 |    | | purine nucleotides de novo biosynthesis 1435709748 | PW000960 |    | | purine nucleotides de novo biosynthesis 2 | PW002033 |    |
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| KEGG Pathways: | |
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| EcoCyc Pathways: | - dTDP-L-rhamnose biosynthesis I DTDPRHAMSYN-PWY
- enterobacterial common antigen biosynthesis ECASYN-PWY
- pyrimidine deoxyribonucleotides de novo biosynthesis I PWY0-166
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| Concentrations |
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| | Concentration | Strain | Media | Growth Status | Growth System | Temperature | Details |
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| 4620± 0 uM | K12 NCM3722 | Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose | Mid-Log Phase | Shake flask and filter culture | 37 oC | PMID: 19561621 | | 525± 0 uM | K12 NCM3722 | Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol | Mid-Log Phase | Shake flask and filter culture | 37 oC | PMID: 19561621 | | 667± 0 uM | K12 NCM3722 | Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate | Mid-Log Phase | Shake flask and filter culture | 37 oC | PMID: 19561621 |
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| Spectra |
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| Spectra: | | Spectrum Type | Description | Splash Key | |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9742300000-c721ba5109dede8a518b | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00dl-9305110000-bbc51754a929afc4eb54 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-0000900000-d176c8e8a9bdb2d457e5 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001i-0000900000-d176c8e8a9bdb2d457e5 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-0900000000-970154df2a1ed9a84a2f | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 15V, negative | splash10-001i-0000900000-50c7a1492866ca00359d | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 18V, negative | splash10-001i-0200900000-dda4f6996cabd8db242f | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 20V, negative | splash10-053r-0602900000-0390bef6ad193f2b5004 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 23V, negative | splash10-0a59-0902600000-2f2a5a489951a9c68992 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 26V, negative | splash10-0a4i-0912200000-1d8c5b170f87fa6f2c9b | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 34V, negative | splash10-0a4i-1921100000-93f84465717aa16d3f7c | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 41V, negative | splash10-0a4i-2920000000-6d1131e45ff20126cf41 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 50V, negative | splash10-0a6r-5910000000-2a9eb44864392efb37c3 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 59V, negative | splash10-056r-9700000000-71a33ac9eaf4e714b558 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 73V, negative | splash10-004i-9200000000-0667d2c3d019b5ca17bc | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - n/a 33V, negative | splash10-001i-0209200000-ed0d460f9e1d08011f06 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - n/a 33V, negative | splash10-004i-9000000000-5ef060d5ec4b80c35c1a | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - n/a 33V, negative | splash10-0a4i-0190000000-e8bf71168cfd7e675dca | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - n/a 33V, negative | splash10-001r-0019000000-d84a6f61ca04e6970204 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 16V, negative | splash10-001i-0009000000-6f966eb3b101b9fadfbe | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 18V, negative | splash10-001i-0019000000-f7153b7fadabb2f7f79f | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-9c496d7377af5eb651b2 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-2901000000-99a48a5d17f022d6494c | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-4900000000-889ecd9966747af96efe | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-053i-1410900000-cc4f8db45f53046b5380 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057r-9870100000-6cf02bd6b66f7b822525 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9100000000-cde9ec4f970230e9f180 | View in MoNA |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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| References |
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| References: | - Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
- Dahlmann N, Ueckermann C: Separation of deoxythymidine-5'-triphosphatase from unspecific hydrolases. A recommended micromethod in the diagnostic evaluation of human carcinoma. Anticancer Res. 1984 Jul-Oct;4(4-5):299-303. Pubmed: 6091528
- Dahlmann N: Human serum thymidine triphosphate nucleotidohydrolase: purification and properties of a new enzyme. Biochemistry. 1982 Dec 21;21(26):6634-9. Pubmed: 6297538
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- Schultes BC, Fischbach E, Dahlmann N: Purification and characterization of two different thymidine-5'-triphosphosphate-hydrolysing enzymes in human serum. Biol Chem Hoppe Seyler. 1992 May;373(5):237-47. Pubmed: 1320895
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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| Synthesis Reference: | Ikehara, Morio; Ohtsuka, Eiko. Coenzyme analogs. XXI. A new synthesis of thymidine 5'-triphosphate and the use of P1,P2-bis(2-cyanoethyl) pyrophosphate in the nucleoside triphosphate synthesis. Chemical & Pharmaceutical Bulletin (1963), 11(11), 1358-63. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| Links |
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| External Links: | |
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