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Chemical Compound Review

dTMP     [(2R,3S,5R)-3-hydroxy-5-(5- methyl-2,4...

Synonyms: Thymidylate, Polythymidine, POLY T, Thymidine 5'MP, Poly(T), ...
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Disease relevance of thymidylic acid

  • I-TevI, the intron-encoded endonuclease from the thymidylate synthase (td) gene of bacteriophage T4, binds its DNA substrate across the minor groove in a sequence-tolerant fashion [1].
  • Rapid characterization of the variable length polythymidine tract in the cystic fibrosis (CFTR) gene: association of the 5T allele with selected CFTR mutations and its incidence in atypical sinopulmonary disease [2].
  • The specificity of a factor-dependent translation system of Escherichia coli was shown to change according to the principle: "either ribo- or deoxyribopolynucleotide messenger". Poly(dT) is shown to be effectively translated in the absence of elongation factors, both at low (2 degrees C) and high (37 degrees C) temperature [3].
  • These data suggest that the 5T polythymidine tract sequence on specific haplotype backgrounds (TG12 and M470V) may cause a low level of full-length functional CFTR protein and CF-like lung disease [4].
  • Effective utilization of exogenous deoxythymidine-5'-monophosphate for DNA synthesis in enterobacteria [5].

High impact information on thymidylic acid

  • We found an inverse relationship between the length of the polythymidine tract at the exon 9 splice branch/acceptor site and the proportion of exon 9- CFTR mRNA transcripts [6].
  • In situ cleavage assays and phasing analyses indicate that upon nicking the bottom strand of the td homing site, I-TevI induces a directed bend of 38 degrees towards the major groove near the cleavage site [1].
  • We demonstrate here that the 28 kDa I-TevI binds the extensive 37 bp td homing site as a monomer and significantly distorts its substrate [1].
  • We measured 20 different hairpin sequences with quasi-random stem sequences that were 6-30 bp long, polythymidine loops that were 3-30 nt long, and stem GC content that ranged from 0% to 100% [7].
  • The 1016-base-pair (bp) intron in the T4 bacteriophage thymidylate synthase gene (td) contains a 735-bp open reading frame that encodes a protein product with endonucleolytic activity [8].

Biological context of thymidylic acid


Anatomical context of thymidylic acid


Associations of thymidylic acid with other chemical compounds

  • A discrete class of strains of Saccharomyces cerevisiae, able to utilize, highly efficiently, exogenous deoxythymidine-5'-monophosphate (dTMP),was found to be sensitive to concentrations greater than 10 Micro M dTMP in an otherwise complete growth medium [15].
  • BACKGROUND: Thymidylate synthase (TS) catalyzes the methylation of deoxyuridine monophosphate (dUMP) to deoxythymidine monophosphate (dTMP) and is a key enzyme for DNA synthesis [16].
  • The TS enzymatic mechanism involves the reductive methylation of the substrate, deoxyuridine monophosphate (dUMP), by transfer of a methylene group from the co-factor, methylenetetrahydrofolate (CH2H4folate), resulting in the production of deoxythymidine monophosphate (dTMP) and dihydrofolate (H2folate) [17].
  • Radiation-generated hydroxyl radicals and hydrogen atoms were shown to induce the cross-linking of polydeoxythymidylic acid (mol X wt approximately 170 000) in N2O-saturated acqueous solution [18].

Gene context of thymidylic acid

  • The endonuclease shows specificity for the intronless form of the td gene [8].
  • This partially purified preparation has been found to contain a DNA endonuclease activity specific for the td delta I gene, which contains a precise deletion of the intron [19].
  • Furthermore, the spin-labeled nucleotide was found to be incorporated internally into polydeoxythymidylic acid via reverse transcriptase to an extent of 1.0 spin-labeled base per 10(3) bases [20].
  • Free radical formation in deoxythymidine-5'-monophosphate gamma-irradiated in frozen solution. A computer-assisted analysis of temperature-dependent ESR spectra [21].
  • Incorporation of low concentrations of TdR requires the T4-induced thymidine kinase (tk) and is not significantly affected by the presence or absence of T4-induced thymidylate synthetase (td) [22].

Analytical, diagnostic and therapeutic context of thymidylic acid


  1. Intron-encoded endonuclease I-TevI binds as a monomer to effect sequential cleavage via conformational changes in the td homing site. Mueller, J.E., Smith, D., Bryk, M., Belfort, M. EMBO J. (1995) [Pubmed]
  2. Rapid characterization of the variable length polythymidine tract in the cystic fibrosis (CFTR) gene: association of the 5T allele with selected CFTR mutations and its incidence in atypical sinopulmonary disease. Friedman, K.J., Heim, R.A., Knowles, M.R., Silverman, L.M. Hum. Mutat. (1997) [Pubmed]
  3. The role of a template sugar-phosphate backbone in the ribosomal decoding mechanism. Comparative study of poly(U) and poly(dT) template activity. Potapov, A.P., Soldatkin, K.A., Soldatkin, A.P., El'skaya, A.V. J. Mol. Biol. (1988) [Pubmed]
  4. Lung disease associated with the IVS8 5T allele of the CFTR gene. Noone, P.G., Pue, C.A., Zhou, Z., Friedman, K.J., Wakeling, E.L., Ganeshananthan, M., Simon, R.H., Silverman, L.M., Knowles, M.R. Am. J. Respir. Crit. Care Med. (2000) [Pubmed]
  5. Effective utilization of exogenous deoxythymidine-5'-monophosphate for DNA synthesis in enterobacteria. Schwan, H., Holldorf, A.W. FEBS Lett. (1975) [Pubmed]
  6. Genetic basis of variable exon 9 skipping in cystic fibrosis transmembrane conductance regulator mRNA. Chu, C.S., Trapnell, B.C., Curristin, S., Cutting, G.R., Crystal, R.G. Nat. Genet. (1993) [Pubmed]
  7. Nanomechanical measurements of the sequence-dependent folding landscapes of single nucleic acid hairpins. Woodside, M.T., Behnke-Parks, W.M., Larizadeh, K., Travers, K., Herschlag, D., Block, S.M. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  8. Characterization of the restriction site of a prokaryotic intron-encoded endonuclease. Chu, F.K., Maley, G., Pedersen-Lane, J., Wang, A.M., Maley, F. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  9. Functional analysis of cis-acting elements regulating the alternative splicing of human CFTR exon 9. Niksic, M., Romano, M., Buratti, E., Pagani, F., Baralle, F.E. Hum. Mol. Genet. (1999) [Pubmed]
  10. Optically detected magnetic resonance of tryptophan residues in Escherichia coli ssb gene product and E. coli plasmid-encoded single-stranded DNA-binding proteins and their complexes with poly(deoxythymidylic) acid. Casas-Finet, J.R., Khamis, M.I., Maki, A.H., Ruvolo, P.P., Chase, J.W. J. Biol. Chem. (1987) [Pubmed]
  11. Increased activities of thymidylate synthetase and thymidine kinase in human thyroid tumors. Sakamoto, S., Murakami, S., Sugawara, M., Mishima, Y., Okamoto, R. Thyroid (1991) [Pubmed]
  12. Alcoholic pancreatitis and polymorphisms of the variable length polythymidine tract in the cystic fibrosis gene. Haber, P.S., Norris, M.D., Apte, M.V., Rodgers, S.C., Norton, I.D., Pirola, R.C., Roberts-Thomson, I.C., Wilson, J.S. Alcohol. Clin. Exp. Res. (1999) [Pubmed]
  13. Covalent attachment of polydeoxythymidylic acid to human erythrocytes. Wennogle, L.P., Berg, H.C. J. Mol. Biol. (1978) [Pubmed]
  14. Poly(dT) inhibition of globin synthesis in the rabbit reticulocyte lysate system. Reversal of the inhibition by poly(dT)-binding protein. Suzuki, H., Mukouyama, E.B. J. Biochem. (1982) [Pubmed]
  15. Nucleic acid metabolism in yeast II. Metabolism of thymidylate during thymidylate excess death. Toper, R., Fäth, W.W., Brendel, M. Mol. Gen. Genet. (1981) [Pubmed]
  16. Significance of thymidylate synthase gene expression level in patients with adenocarcinoma of the lung. Hashimoto, H., Ozeki, Y., Sato, M., Obara, K., Matsutani, N., Nakagishi, Y., Ogata, T., Maehara, T. Cancer (2006) [Pubmed]
  17. The complex of the anti-cancer therapeutic, BW1843U89, with thymidylate synthase at 2.0 A resolution: implications for a new mode of inhibition. Stout, T.J., Stroud, R.M. Structure (1996) [Pubmed]
  18. Free radical-induced cross-linking of polydeoxythymidylic acid in deoxygenated aqueous solution. Karam, L.R., Simic, M.G., Dizdaroglu, M. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. (1986) [Pubmed]
  19. Evidence that the intron open reading frame of the phage T4 td gene encodes a specific endonuclease. West, D.K., Changchien, L.M., Maley, G.F., Maley, F. J. Biol. Chem. (1989) [Pubmed]
  20. Interaction of polymerases with 2'-deoxyuridine-5'-triphosphate spin-labeled at the 5-position. Warwick-Koochaki, P.E., Hakan, A., Bobst, A.M. FEBS Lett. (1983) [Pubmed]
  21. Free radical formation in deoxythymidine-5'-monophosphate gamma-irradiated in frozen solution. A computer-assisted analysis of temperature-dependent ESR spectra. Gregoli, S., Olast, M., Bertinchamps, A. Radiat. Res. (1976) [Pubmed]
  22. Incorporation of thymine-containing DNA precursors in wild-type and mutant T4-infected plasmolysed cells. Melamede, R.J., Wallace, S.S. Mol. Gen. Genet. (1983) [Pubmed]
  23. Development of a microcapillary column for detecting targeted messenger RNA molecules. Ohnishi, M. Journal of chromatography. A. (2006) [Pubmed]
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