Thymidine monophosphate

Thymidine monophosphate

Names
IUPAC name Thymidine monophosphate
Other names 5'-Thymidylic acid
Identifiers
CAS Number	365-07-1  Y
3D model (JSmol)	Interactive image
Abbreviations	dTMP
Beilstein Reference	3916216
ChEBI	CHEBI:26999  Y
ChEMBL	ChEMBL394429  N
ChemSpider	10239189  Y
PubChem CID	16755631
UNII	43W3021X6C  Y
CompTox Dashboard (EPA)	DTXSID001310498
InChI InChI=1S/C10H15N2O8P/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(20-8)4-19-21(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,17,18)/p-2 N Key: GYOZYWVXFNDGLU-UHFFFAOYSA-L N
SMILES Cc1cn([C@H]2C[C@H](O)[C@@H](COP([O-])([O-])=O)O2)c(=O)[nH]c1=O
Properties
Chemical formula	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). N  verify  (what is  YN ?) Infobox references

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

• DNA
• Nucleoside
• Nucleotide
• Oligonucleotide
• RNA

References

1. 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.
2. Elsevier, Dorland's Illustrated Medical Dictionary, Elsevier.
3. 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
4. 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.
5. 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.
6. 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.