Thymidine monophosphate

{{Technical|date=April 2022}} {{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470609635 | ImageFile = DTMP_chemical_structure.svg | ImageFile_Ref = {{chemboximage|correct|??}} | ImageSize = 150 | ImageAlt = Skeletal formula of thymidine monophosphate as an anion, single negative charge | ImageFile1 = Deoxythymidine monophosphate anion 3D spacefill.png | ImageSize1 = 170 | ImageAlt1 = Space-filling model of the thymidine monophosphate molecule as an anion, double negative charge | IUPACName = Thymidine monophosphate | OtherNames = 5'-Thymidylic acid |Section1={{Chembox Identifiers | CASNo = 365-07-1 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 43W3021X6C | Abbreviations = dTMP | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 394429 | PubChem = 16755631 | ChemSpiderID = 10239189 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 26999 | Beilstein = 3916216 | SMILES = Cc1cn([C@H]2C[C@H](O)[C@@H](COP([O-])([O-])=O)O2)c(=O)[nH]c1=O | StdInChI = 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 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = GYOZYWVXFNDGLU-UHFFFAOYSA-L | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} }} |Section2={{Chembox Properties | Formula = C10H15N2O8P | MolarMass = 322.2085 g mol−1 }} }}

'''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").<ref>{{cite book|title=The ACS style guide: effective communication of scientific information|year=2006|publisher=American Chemical Society|location=Washington, D.C.|isbn=978-0-8412-3999-9|edition=3rd|editor1=Coghill, Anne M.|editor2=Garson, Lorrin R.|page=[https://archive.org/details/acsstyleguideeff0000unse/page/244 244]|url=https://archive.org/details/acsstyleguideeff0000unse/page/244}}</ref> ''Dorland’s Illustrated Medical Dictionary''<ref name="Dorlands">{{Citation |author=Elsevier |authorlink=Elsevier |title=Dorland's Illustrated Medical Dictionary |publisher=Elsevier |url=http://dorlands.com/ |postscript=.}}</ref> 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.<ref>{{Citation |last1=Field |first1=Martha S |title=Thymidylate Synthesis |date=2016 |encyclopedia=Encyclopedia of Life Sciences |pages=1–7 |url=https://onlinelibrary.wiley.com/doi/abs/10.1002/9780470015902.a0001397.pub3 |access-date=2025-12-09 |publisher=John Wiley & Sons, Ltd |language=en |doi=10.1002/9780470015902.a0001397.pub3 |isbn=978-0-470-01590-2 |last2=Stover |first2=Patrick J |last3=Kisliuk |first3=Roy|url-access=subscription }}</ref> 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.<ref>{{Cite journal |last1=Mankoff |first1=David A. |last2=Shields |first2=Anthony F. |last3=Krohn |first3=Kenneth A. |date=2005-01-01 |title=PET imaging of cellular proliferation |url=https://www.radiologic.theclinics.com/article/S0033-8389(04)00182-4/abstract |journal=Radiologic Clinics |language=English |volume=43 |issue=1 |pages=153–167 |doi=10.1016/j.rcl.2004.09.005 |pmid=15693654 |issn=0033-8389}}</ref>

== 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.<ref>{{Cite journal |last1=Chen |first1=Yen-Ling |last2=Eriksson |first2=Staffan |last3=Chang |first3=Zee-Fen |date=2010-08-27 |title=Regulation and functional contribution of thymidine kinase 1 in repair of DNA damage |journal=The Journal of Biological Chemistry |volume=285 |issue=35 |pages=27327–27335 |doi=10.1074/jbc.M110.137042 |doi-access=free |issn=1083-351X |pmc=2930731 |pmid=20554529}}</ref> 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.<ref>{{Cite journal |last1=Hu |first1=Chun-Mei |last2=Tsao |first2=Ning |last3=Wang |first3=Yi-Ting |last4=Chen |first4=Yu-Ju |last5=Chang |first5=Zee-Fen |date=2019 |title=Thymidylate kinase is critical for DNA repair via ATM-dependent Tip60 complex formation |journal=The FASEB Journal |language=en |volume=33 |issue=2 |pages=2017–2025 |doi=10.1096/fj.201800856R |pmid=30199284 |doi-access=free |issn=1530-6860}}</ref>

== See also == * DNA * Nucleoside * Nucleotide * Oligonucleotide * RNA

==References== {{reflist}}

Category:Nucleotides Category:Organophosphates