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Chemical Compound Review

Miazine     pyrimidine

Synonyms: pyrimidin, PYRIMIDINE, Metadiazine, m-Diazine, SureCN1846, ...
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Disease relevance of pyrimidine


Psychiatry related information on pyrimidine


High impact information on pyrimidine


Chemical compound and disease context of pyrimidine

  • From the fact that certain RNAs, particularly single-stranded, pyrimidine-rich polymers containing at least 10% cytidylate residues, are more effective than other RNAs at promoting rho-ATPase, it has been proposed that rho recognises specific sites oion on a mRNA transcribed from bacteriophage lambda DNA [14].
  • The ability to excise (repair) UV-induced pyrimidine dimers in Escherichia coli is not related to its ability to remove N-methyl-N'-nitro-N-nitrosoguanidine (MNNG)-induced O6-methylguanine (O6-MeG) from DNA [15].
  • BACKGROUND: High-protein diets have been found to protect mice from the lethal effects of cytotoxic pyrimidine analogues and to reduce the toxicity of the antipyrimidine fluorouracil (5-FU), but the biochemical explanation for these effects is not known [16].
  • Infected-cell protein 4 (ICP4), the major regulatory protein specified by herpes simplex virus 1 in infected cells, binds to homologs of the sequence ATCGTCnnnnYCGRC (A sites, where n is any nucleotide, Y is a pyrimidine, and R is a purine) and to unrelated sequences for which no consensus sequence has been derived (B sites) [17].
  • The application of T4 endonuclease V encapsulated in liposomes to UV-irradiated mouse skin decreased the number of cyclobutane pyrimidine dimers in the epidermis and prevented suppression of both delayed and contact hypersensitivity responses [18].

Biological context of pyrimidine

  • This secondary methylation is apparently restricted to a particular subclass of mRNAs having a high frequency of pyrimidine nucleotides at position Y, a composition at position X which differs from that of the bulk of the cap I-terminated mRNAs, and a relatively slow rate of turnover [19].
  • Our findings support the concept that clusters of similar purine or pyrimidine residues exist along the arms of condensed metaphase chromosomes, with the possibility that concentrations of 5-methylcytosine residues might have been enhanced at the surface of the chromosomes during the condensation process [20].
  • Kuchino et al. studied DNA synthesis on oligodeoxynucleotide templates containing 8-oxodG, concluding that the modified base lacked base pairing specificity and directed misreading of pyrimidine residues neighbouring the lesion [21].
  • The ultraviolet irradiation maximally induces the defence genes at levels where cyclobutane pyrimidine dimer formation, an indicator of DNA damage, is less than 0.2 dimers per gene [22].
  • By analysing the photofootprints of fragments produced by cleavage of the DNA chain near [6-4]-pyrimidine dimers, we show here that a homopurine-homopyrimidine insert (with either d(TC)x or d(C)n) in plasmid pUC19 is, as expected, a good target for UV-induced pyrimidine-dimer formation [23].

Anatomical context of pyrimidine


Associations of pyrimidine with other chemical compounds


Gene context of pyrimidine

  • NF-kappaB specifically recognizes kappaB DNA elements with a consensus sequence of 5'-GGGRNYYYCC-3' (R is an unspecified purine; Y is an unspecified pyrimidine; and N is any nucleotide) [33].
  • Regulatory factor X (RFX) proteins are transcriptional activators that recognize X-boxes (DNA of the sequence 5'-GTNRCC(0-3N)RGYAAC-3', where N is any nucleotide, R is a purine and Y is a pyrimidine) using a highly conserved 76-residue DNA-binding domain (DBD) [34].
  • The uninducible phenotype of this mutant is completely suppressed by an ochre suppressor, strengthening the hypothesis that PPR2 acts on URA4 transcription through the synthesis of a regulatory protein [35].
  • A regulatory gene PPR2 (pyrimidine pathway regulatory 2) acting specifically on this step, has been characterized, cloned and sequenced [35].
  • A p53-dependent S-phase checkpoint helps to protect cells from DNA damage in response to starvation for pyrimidine nucleotides [36].

Analytical, diagnostic and therapeutic context of pyrimidine


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  2. Atomic model of a pyrimidine dimer excision repair enzyme complexed with a DNA substrate: structural basis for damaged DNA recognition. Vassylyev, D.G., Kashiwagi, T., Mikami, Y., Ariyoshi, M., Iwai, S., Ohtsuka, E., Morikawa, K. Cell (1995) [Pubmed]
  3. Complementation of the xeroderma pigmentosum DNA repair defect in cell-free extracts. Wood, R.D., Robins, P., Lindahl, T. Cell (1988) [Pubmed]
  4. RNA recognition by Tat-derived peptides: interaction in the major groove? Weeks, K.M., Crothers, D.M. Cell (1991) [Pubmed]
  5. Cleavage of pyrimidine dimers in specific DNA sequences by a pyrimidine dimer DNA-glycosylase of M. luteus. Haseltine, W.A., Gordon, L.K., Lindan, C.P., Grafstrom, R.H., Shaper, N.L., Grossman, L. Nature (1980) [Pubmed]
  6. Mitochondrial and herpesvirus-specific deoxypyrimidine kinases. Leung, W.C., Dubbs, D.R., Trkula, D., Kit, S. J. Virol. (1975) [Pubmed]
  7. Stavudine and the peripheral nerve in HIV-1 infected patients. von Giesen, H.J., Hefter, H., Jablonowski, H., Arendt, G. J. Neurol. (1999) [Pubmed]
  8. Montmorillonite catalysis of 30-50 mer oligonucleotides: laboratory demonstration of potential steps in the origin of the RNA world. Ferris, J.P. Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life. (2002) [Pubmed]
  9. Memory deficits of aged male rats can be improved by pyrimidine nucleosides and n-acetyl-glutamine. Drago, F., D'Agata, V., Valerio, C., Spadaro, F., Raffaele, R., Nardo, L., Grassi, M., Freni, V. Clinical neuropharmacology. (1990) [Pubmed]
  10. Excessive glutamine sensitivity in Alzheimer's disease and Down syndrome lymphocytes. Peeters, M.A., Salabelle, A., Attal, N., Rethore, M.O., Mircher, C., Laplane, D., Lejeune, J. J. Neurol. Sci. (1995) [Pubmed]
  11. Selective removal of transcription-blocking DNA damage from the transcribed strand of the mammalian DHFR gene. Mellon, I., Spivak, G., Hanawalt, P.C. Cell (1987) [Pubmed]
  12. Differential DNA repair in transcriptionally active and inactive proto-oncogenes: c-abl and c-mos. Madhani, H.D., Bohr, V.A., Hanawalt, P.C. Cell (1986) [Pubmed]
  13. DNA repair in an active gene: removal of pyrimidine dimers from the DHFR gene of CHO cells is much more efficient than in the genome overall. Bohr, V.A., Smith, C.A., Okumoto, D.S., Hanawalt, P.C. Cell (1985) [Pubmed]
  14. A rho-recognition site on phage lambda cro-gene mRNA. Bektesh, S.L., Richardson, J.P. Nature (1980) [Pubmed]
  15. Removal of O6-methylguanine from DNA of normal and xeroderma pigmentosum-derived lymphoblastoid lines. Sklar, R., Strauss, B. Nature (1981) [Pubmed]
  16. Effect of high-protein diet on pyrimidine synthesis and response to PALA in mouse tissues. Zaharevitz, D.W., Grubb, M.F., Hyman, R., Chisena, C., Cysyk, R.L. J. Natl. Cancer Inst. (1993) [Pubmed]
  17. Binding of the herpes simplex virus major regulatory protein to viral DNA. Michael, N., Roizman, B. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  18. Pyrimidine dimers in DNA initiate systemic immunosuppression in UV-irradiated mice. Kripke, M.L., Cox, P.A., Alas, L.G., Yarosh, D.B. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  19. Kinetics of formation of 5' terminal caps in mRNA. Perry, R.P., Kelley, D.E. Cell (1976) [Pubmed]
  20. Localization of 5-methylcytosine in human metaphase chromosomes by immunoelectron microscopy. Lubit, B.W., Pham, T.D., Miller, O.J., Erlanger, B.F. Cell (1976) [Pubmed]
  21. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Shibutani, S., Takeshita, M., Grollman, A.P. Nature (1991) [Pubmed]
  22. The octadecanoid signalling pathway in plants mediates a response to ultraviolet radiation. Conconi, A., Smerdon, M.J., Howe, G.A., Ryan, C.A. Nature (1996) [Pubmed]
  23. Protection against UV-induced pyrimidine dimerization in DNA by triplex formation. Lyamichev, V.I., Frank-Kamenetskii, M.D., Soyfer, V.N. Nature (1990) [Pubmed]
  24. Purine and pyrimidine mononucleotides depolarise neurones of explanted amphibian sympathetic ganglia. Siggins, G.R., Gruol, D.L., Padjen, A.L., Formans, D.S. Nature (1977) [Pubmed]
  25. Dark-repair of ultraviolet-induced pyrimidine dimers in the DNA of wild carrot protoplasts. Howland, G.P. Nature (1975) [Pubmed]
  26. A thymus-specific member of the HMG protein family regulates the human T cell receptor C alpha enhancer. Waterman, M.L., Fischer, W.H., Jones, K.A. Genes Dev. (1991) [Pubmed]
  27. The carboxyl terminus of vertebrate poly(A) polymerase interacts with U2AF 65 to couple 3'-end processing and splicing. Vagner, S., Vagner, C., Mattaj, I.W. Genes Dev. (2000) [Pubmed]
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  29. Embryonic folate metabolism and mouse neural tube defects. Fleming, A., Copp, A.J. Science (1998) [Pubmed]
  30. The structure of flavocytochrome c sulfide dehydrogenase from a purple phototrophic bacterium. Chen, Z.W., Koh, M., Van Driessche, G., Van Beeumen, J.J., Bartsch, R.G., Meyer, T.E., Cusanovich, M.A., Mathews, F.S. Science (1994) [Pubmed]
  31. Induction of differentiation of human promyelocytic leukemia cells (HL-60) by nucleosides and methotrexate. Bodner, A.J., Ting, R.C., Gallo, R.C. J. Natl. Cancer Inst. (1981) [Pubmed]
  32. Canine cyclic hematopoiesis is associated with abnormal purine and pyrimidine metabolism. Osborne, W.R., Hammond, W.P., Dale, D.C. J. Clin. Invest. (1983) [Pubmed]
  33. Crystal structure of p50/p65 heterodimer of transcription factor NF-kappaB bound to DNA. Chen, F.E., Huang, D.B., Chen, Y.Q., Ghosh, G. Nature (1998) [Pubmed]
  34. Structure of the winged-helix protein hRFX1 reveals a new mode of DNA binding. Gajiwala, K.S., Chen, H., Cornille, F., Roques, B.P., Reith, W., Mach, B., Burley, S.K. Nature (2000) [Pubmed]
  35. Complete sequence of a eukaryotic regulatory gene. Hubert, J.C., Guyonvarch, A., Kammerer, B., Exinger, F., Liljelund, P., Lacroute, F. EMBO J. (1983) [Pubmed]
  36. A p53-dependent S-phase checkpoint helps to protect cells from DNA damage in response to starvation for pyrimidine nucleotides. Agarwal, M.L., Agarwal, A., Taylor, W.R., Chernova, O., Sharma, Y., Stark, G.R. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  37. De novo pyrimidine biosynthesis is required for virulence of Toxoplasma gondii. Fox, B.A., Bzik, D.J. Nature (2002) [Pubmed]
  38. Ligation of oligonucleotides by pyrimidine dimers--a missing 'link' in the origin of life? Lewis, R.J., Hanawalt, P.C. Nature (1982) [Pubmed]
  39. Multiple DNA sequence elements are necessary for the function of an immunoglobulin heavy chain promoter. Eaton, S., Calame, K. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  40. A combined kinetic and modeling study of the catalytic center subsites of human angiogenin. Russo, N., Acharya, K.R., Vallee, B.L., Shapiro, R. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
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