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Chemical Compound Review

dUMP     [(2R,3S,5R)-5-(2,4- dioxopyrimidin-1-yl)-3...

Synonyms: deoxyuridylate, Deoxy-UMP, SureCN8200, CHEMBL211312, CHEBI:17622, ...
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Disease relevance of UMP


High impact information on UMP


Chemical compound and disease context of UMP


Biological context of UMP


Anatomical context of UMP


Associations of UMP with other chemical compounds

  • Fluorodeoxyuridylate (FdUMP) was assayed by isotope dilution of [3H]FdUMP binding to bacterial TS; free and total TS was determined by [3H]FdUMP binding; and deoxyuridylate (dUMP) was assayed by conversion to [14C]thymidylate [20].
  • The structural evidence reveals that upon binding cofactor analogue and forming a covalent bond from the nucleophilic cysteine to the substrate, dUMP, at one active site, PcTS undergoes a conformational change that renders the opposite monomer incapable of forming a covalent bond or binding a molecule of cofactor analogue [21].
  • Following electroporation, cells were shown to be fully functional as monitored by the incorporation of deoxyuridylate, after conversion to thymidylate, into DNA [22].
  • Invariant arginine 179, one of four arginines that are conserved in all thymidylate synthases (TS) and that bind the phosphate moiety of the substrate 2'-deoxyuridine-5'-monophosphate (dUMP), can be altered even to a negatively charged glutamic acid with little effect on kcat [23].
  • The assay is based on the separation of the substrate, deoxyuridylate (dUMP), and its product, deoxythymidylate (dTMP), on a LiChrosorb RP-8 reversed-phase column with 44 mM triethylammonium phosphate (pH 7.0) as mobile phase and a flow-rate of 1.0 ml/min [24].

Gene context of UMP


Analytical, diagnostic and therapeutic context of UMP


  1. Asn177 in Escherichia coli thymidylate synthase is a major determinant of pyrimidine specificity. Hardy, L.W., Nalivaika, E. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  2. Kinetics and mechanism of interaction of 10-propargyl-5,8-dideazafolate with thymidylate synthase. Pogolotti, A.L., Danenberg, P.V., Santi, D.V. J. Med. Chem. (1986) [Pubmed]
  3. Observations on the mechanisms underlying the defective methylation of deoxyuridylate in kwashiorkor. Wickramasinghe, S.N., Litwinczuk, R.A., Akinyanju, O.O., Grange, A. Br. J. Haematol. (1983) [Pubmed]
  4. Cloning, expression, purification, and characterization of 2'-deoxyuridylate hydroxymethylase from phage SPO1. Schellenberger, U., Livi, L.L., Santi, D.V. Protein Expr. Purif. (1995) [Pubmed]
  5. Binding of 5-fluorodeoxyuridylate to thymidylate synthase in human colon adenocarcinoma xenografts. Houghton, J.A., Torrance, P.M., Radparvar, S., Williams, L.G., Houghton, P.J. European journal of cancer & clinical oncology. (1986) [Pubmed]
  6. An uncommon nucleotide conformation shown by molecular structure of deoxyuridine-5'-phosphate and nucleic acid stereochemistry. Viswamitra, M.A., Seshadri, T.P., Post, M.L. Nature (1975) [Pubmed]
  7. Crystal structure of deoxycytidylate hydroxymethylase from bacteriophage T4, a component of the deoxyribonucleoside triphosphate-synthesizing complex. Song, H.K., Sohn, S.H., Suh, S.W. EMBO J. (1999) [Pubmed]
  8. Biochemical determinants of tumor sensitivity to 5-fluorouracil: ultrasensitive methods for the determination of 5-fluoro-2'-deoxyuridylate, 2'-deoxyuridylate, and thymidylate synthetase. Moran, R.G., Spears, C.P., Heidelberger, C. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  9. Entropy in bi-substrate enzymes: proposed role of an alternate site in chaperoning substrate into, and products out of, thymidylate synthase. Birdsall, D.L., Finer-Moore, J., Stroud, R.M. J. Mol. Biol. (1996) [Pubmed]
  10. Role of the conserved tryptophan 82 of Lactobacillus casei thymidylate synthase. Kealey, J.T., Eckstein, J., Santi, D.V. Chem. Biol. (1995) [Pubmed]
  11. Structural basis for recognition of polyglutamyl folates by thymidylate synthase. Kamb, A., Finer-Moore, J., Calvert, A.H., Stroud, R.M. Biochemistry (1992) [Pubmed]
  12. Crystal structures of thymidylate synthase mutant R166Q: structural basis for the nearly complete loss of catalytic activity. Sotelo-Mundo, R.R., Changchien, L., Maley, F., Montfort, W.R. J. Biochem. Mol. Toxicol. (2006) [Pubmed]
  13. DNA fragmentation and cytotoxicity from increased cellular deoxyuridylate. Ingraham, H.A., Dickey, L., Goulian, M. Biochemistry (1986) [Pubmed]
  14. Cross-resistance to antifolates in multidrug resistant cell lines with P-glycoprotein or multidrug resistance protein expression. van Triest, B., Pinedo, H.M., Telleman, F., van der Wilt, C.L., Jansen, G., Peters, G.J. Biochem. Pharmacol. (1997) [Pubmed]
  15. Thymidylate synthase: a novel genetic determinant of plasma homocysteine and folate levels. Trinh, B.N., Ong, C.N., Coetzee, G.A., Yu, M.C., Laird, P.W. Hum. Genet. (2002) [Pubmed]
  16. Biochemical effects of folate-based inhibitors of thymidylate synthase in MGH-U1 cells. Mitrovski, B., Pressacco, J., Mandelbaum, S., Erlichman, C. Cancer Chemother. Pharmacol. (1994) [Pubmed]
  17. Primary structure of cyclohydrolase (Mch) from Methanobacterium thermoautotrophicum (strain Marburg) and functional expression of the mch gene in Escherichia coli. Vaupel, M., Dietz, H., Linder, D., Thauer, R.K. Eur. J. Biochem. (1996) [Pubmed]
  18. Mutants of Chinese hamster cells deficient in thymidylate synthetase. Li, I.C., Chu, E.H. J. Cell. Physiol. (1984) [Pubmed]
  19. Studies of erythroblast function in congenital dyserythropoietic anaemia, type I: evidence of impaired DNA, RNA, and protein synthesis and unbalanced globin chain synthesis in ultrastructurally abnormal cells. Wickramasinghe, S.N., Pippard, M.J. J. Clin. Pathol. (1986) [Pubmed]
  20. Mechanisms of innate resistance to thymidylate synthase inhibition after 5-fluorouracil. Spears, C.P., Gustavsson, B.G., Berne, M., Frösing, R., Bernstein, L., Hayes, A.A. Cancer Res. (1988) [Pubmed]
  21. The structural mechanism for half-the-sites reactivity in an enzyme, thymidylate synthase, involves a relay of changes between subunits. Anderson, A.C., O'Neil, R.H., DeLano, W.L., Stroud, R.M. Biochemistry (1999) [Pubmed]
  22. Use of electroporation to study the cytotoxic effects of fluorodeoxyuridylate in intact cells. Jastreboff, M.M., Sokoloski, J.A., Bertino, J.R., Narayanan, R. Biochem. Pharmacol. (1987) [Pubmed]
  23. Contribution of a salt bridge to binding affinity and dUMP orientation to catalytic rate: mutation of a substrate-binding arginine in thymidylate synthase. Finer-Moore, J.S., Fauman, E.B., Morse, R.J., Santi, D.V., Stroud, R.M. Protein Eng. (1996) [Pubmed]
  24. High-performance liquid chromatographic assay for thymidylate synthase from the human malaria parasite, Plasmodium falciparum. Krungkrai, J., Yuthavong, Y., Webster, H.K. J. Chromatogr. (1989) [Pubmed]
  25. Effects of 5,8-dideazaisopteroylglutamate and its possible tri-gamma-glutamyl metabolite (5,8-dideazaisoPteGlu3) on colon adenocarcinoma, and the folate dependent enzymes thymidylate synthase and dihydrofolate reductase. Fernandes, D.J., Cardenas, R.M., Bertino, J.R., Hynes, J.B. Adv. Exp. Med. Biol. (1983) [Pubmed]
  26. Studies on the interaction with thymidylate synthase of analogues of 2'-deoxyuridine-5'-phosphate and 5-fluoro-2'-deoxyuridine-5'-phosphate with modified phosphate groups. Rode, W., Kulikowski, T., Kedzierska, B., Shugar, D. Biochem. Pharmacol. (1987) [Pubmed]
  27. 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]
  28. Detection of thymidylate synthase gene expression levels in formalin-fixed paraffin embedded tissue by semiquantitative, nonradioactive reverse transcriptase polymerase chain reaction. Houze, T.A., Larsson, L., Larsson, P.A., Hansson, G., Gustavsson, B. Tumour Biol. (1997) [Pubmed]
  29. The SO4-.-induced oxidation of 2'-deoxyuridine-5'-phosphate, uridine-5'-phosphate and thymidine-5'-phosphate. An ESR study in aqueous solution. Hildenbrand, K. Z. Naturforsch., C, J. Biosci. (1990) [Pubmed]
  30. Therapeutic response of leukemic mice treated with fluorinated pyrimidines and inhibitors of deoxyuridylate synthesis. Moran, R.G., Danenberg, P.V., Heidelberger, C. Biochem. Pharmacol. (1982) [Pubmed]
  31. Auger effects on bromo-deoxyuridine-monophosphate irradiated with monochromatic X-rays around bromine K-absorption edge. Takakura, K. Radiation and environmental biophysics. (1989) [Pubmed]
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