Thymidine monophosphate
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| Names | |
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| IUPAC name
Thymidine monophosphate
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| Other names
5'-Thymidylic acid
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | dTMP |
| 3916216 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C10H15N2O8P | |
| Molar mass | 322.2085 g mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thymidine monophosphate (TMP), also known as thymidylic acid (conjugate base thymidylate), deoxythymidine monophosphate (dTMP), or deoxythymidylic acid (conjugate base deoxythymidylate), is a nucleotide that is used as a monomer in DNA. It is an ester of phosphoric acid with the nucleoside thymidine. dTMP consists of a phosphate group, the pentose sugar deoxyribose, and the nucleobase thymine. Unlike the other deoxyribonucleotides, thymidine monophosphate often does not contain the "deoxy" prefix in its name; nevertheless, its symbol often includes a "d" ("dTMP").[1] Dorland’s Illustrated Medical Dictionary[2] provides an explanation of the nomenclature variation at its entry for thymidine.
As a substituent, it is called by the prefix thymidylyl-.
Thymidine monophosphate formation
Cells utilize two separate pathways to produce thymidine monophosphate. One of these pathways is a salvage pathway. In the salvage pathway, thymidine (dT) undergoes phosphorylation by the enzyme TK1.[3] By phosphorylating dT, TK1 adds a phosphate group to dT, resulting in dTMP. The other pathway that leads to the formation of TMP is a de novo, pathway. During the de novo pathway, dTMP is formed from the nucleotide deoxyuridine monophosphate (dUMP). In this pathway, thymidylate synthase (TS) adds a methyl group to deoxyuridine monophosphate to form dTMP.[4]
Uses in DNA
Following its synthesis by the salvage or de novo pathways, dTMP then goes through a series of phosphorylations that result in the deoxythymidine triphosphates (dTTP) that are vital in the synthesis of DNA. Deoxynucleotides (dNTPs) are used in the synthesis of DNA, and dTMP is a precursor to one of the dNTPs, dTTP. In cells, dTMP is synthesized into deoxythymidine diphosphate (dTDP) using thymidylate kinase. From dTDP, dTTP is then synthesized using a nucleotide diphosphate kinase. The dTTP that is synthesized from dTMPs are used in DNA synthesis in both the mitochondria and the cytosol.[5] In addition to its role in DNA synthesis, dTTP is also a requisite for DNA repair, thus indicating the importance of dTMP in the synthesis and repair of DNA.[6]
See also
References
- ^ Coghill, Anne M.; Garson, Lorrin R., eds. (2006). The ACS style guide: effective communication of scientific information (3rd ed.). Washington, D.C.: American Chemical Society. p. 244. ISBN 978-0-8412-3999-9.
- ^ Elsevier, Dorland's Illustrated Medical Dictionary, Elsevier.
- ^ Field, Martha S; Stover, Patrick J; Kisliuk, Roy (2016), "Thymidylate Synthesis", Encyclopedia of Life Sciences, John Wiley & Sons, Ltd, pp. 1–7, doi:10.1002/9780470015902.a0001397.pub3, ISBN 978-0-470-01590-2, retrieved 2025-12-09
- ^ Mankoff, David A.; Shields, Anthony F.; Krohn, Kenneth A. (2005-01-01). "PET imaging of cellular proliferation". Radiologic Clinics. 43 (1): 153–167. doi:10.1016/j.rcl.2004.09.005. ISSN 0033-8389. PMID 15693654.
- ^ Chen, Yen-Ling; Eriksson, Staffan; Chang, Zee-Fen (2010-08-27). "Regulation and functional contribution of thymidine kinase 1 in repair of DNA damage". The Journal of Biological Chemistry. 285 (35): 27327–27335. doi:10.1074/jbc.M110.137042. ISSN 1083-351X. PMC 2930731. PMID 20554529.
- ^ Hu, Chun-Mei; Tsao, Ning; Wang, Yi-Ting; Chen, Yu-Ju; Chang, Zee-Fen (2019). "Thymidylate kinase is critical for DNA repair via ATM-dependent Tip60 complex formation". The FASEB Journal. 33 (2): 2017–2025. doi:10.1096/fj.201800856R. ISSN 1530-6860. PMID 30199284.