Thymidine monophosphate
Chemical compound
From Wikipedia, the free encyclopedia
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.
| |
 | |
| Names | |
|---|---|
| IUPAC name
Thymidine monophosphate | |
| Other names
5'-Thymidylic acid | |
| Identifiers | |
3D model (JSmol) |
|
| Abbreviations | dTMP |
| 3916216 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| 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).
| |
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]