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Chemical Compound Review

AC1LA63C     [5-(4-amino-2-oxo-pyrimidin- 1-yl)-3-[[3...

Synonyms: 5'-pCAC-3'
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Disease relevance of Trinucleotides


Psychiatry related information on Trinucleotides

  • Huntington's disease and repeating trinucleotides [6].
  • We thus cannot conclude that CAG/CTG trinucleotides are involved in psychotic disorders and that either the differences observed in similar studies may be the result of population stratification, or that the increased frequency of larger repeats amongst affected individuals is a much smaller effect than previously thought [7].

High impact information on Trinucleotides

  • RESULTS: One hundred forty of the 187 patients, with ages at onset ranging from 2 to 51 years, were homozygous for a GAA expansion that had 120 to 1700 repeats of the trinucleotides [8].
  • Analysis of 84 human X chromosomes for the presence of interrupting AGG trinucleotides within the CGG repeat tract of the FMR1 gene revealed that most alleles possess two interspersed AGGs and that the longest tract of uninterrupted CGG repeats is usually found at the 3' end [9].
  • We now find that certain di- and trinucleotides with free 3' hydroxyl groups reopen the circular IVS at the cyclization junction, producing a linear molecule with the oligonucleotide covalently attached to its 5' end [10].
  • Loss-of-function kryptonite alleles resemble mutants in the DNA methyltransferase gene CHROMOMETHYLASE3 (CMT3), showing loss of cytosine methylation at sites of CpNpG trinucleotides (where N is A, C, G or T) and reactivation of endogenous retrotransposon sequences [11].
  • The results show how modular finger interactions with trinucleotides can be used, in conjunction with alternative splicing, to alter the binding specificity and increase the spectrum of sites recognized by a DNA binding domain [12].

Chemical compound and disease context of Trinucleotides


Biological context of Trinucleotides

  • The results are consistent with modular interactions between zinc fingers and trinucleotides and also suggest rules for recognition of AT-rich DNA sites by zinc finger proteins [12].
  • During the second phase, the nucleotide sequences of RNA codons were deciphered by determining the species of aminoacyl-tRNA that bound to ribosomes in response to trinucleotides of known sequence [14].
  • Because the experimental support for the C(II)(oligo) rule is much less complete, the present article, focusing on the special case of trinucleotides (triplets), examined several gigabases of genome sequences from a wide range of species and kingdoms including organelles such as mitochondria and chloroplasts [15].
  • RNA helical oligonucleotides that recapitulate the acceptor stems of transfer RNAs, and that are devoid of the anticodon trinucleotides of the genetic code, are aminoacylated by aminoacyl tRNA synthetases [16].
  • Oligonucleotides that recapitulate the acceptor stems of tRNAs are substrates for aminoacylation by many tRNA synthetases in vitro, even though these substrates are missing the anticodon trinucleotides of the genetic code [17].

Anatomical context of Trinucleotides

  • The Xi in normal female lymphocytes is also highly methylated, but some GCG or CGC trinucleotides partially escape methylation; all other CpGs are fully methylated [18].
  • It was also demonstrated that ODN 2006, a widely used immunostimulant of human B cells, possess two kinds of immunostimulatory motifs: one of them mainly composed of two successive TCG trinucleotides located at the 5' end and another one (duplicated) of the PyNTTTTGT kind here described [19].
  • The localized NPPase activity around the regressing Mullerian duct suggests that NPPase may appear as a consequence of duct regression and may act to control the degree of membrane phosphorylation by degrading excess trinucleotides [20].
  • High levels (200 microM) of CpA or the trinucleotides containing CpA have no effect on translation in a wheat germ cell-free system [21].
  • Application to the cytosolic side of inside-out patches of Na+ ions, mono- di- and trinucleotides, taurine, reduced and oxidized forms of glutathione, or peptides extracted from pulmonary artery smooth muscle, did not reproduce the inward rectification [22].

Associations of Trinucleotides with other chemical compounds


Gene context of Trinucleotides

  • In patients with PD, the presence of two long alleles, with more than 16 repeated AAT trinucleotides in the CNR1 gene, was associated with a reduced prevalence of depression (Fisher's exact test: P=0.003) [28].
  • Meta-analysis demonstrated that the preferentially altered sequence motifs of BCL6 in PMBL were TA (p=0.002) and AT (p=0.0008) dinucleotides and TAT trinucleotides (p=0.001) [29].
  • Diversity was created by replacing the V(H) and V(L) CDR3 regions of the master genes by CDR3 library cassettes, generated from mixed trinucleotides and biased towards natural human antibody CDR3 sequences [30].
  • A new class of disease (including Huntington disease, Kennedy disease, and spinocerebellar ataxias types 1 and 3) results from abnormal expansions of CAG trinucleotides in the coding regions of genes [31].
  • The following types of motifs in that portion are analyzed: (i) concatamers of mono-, di-, and trinucleotides; (ii) tightly clustered hexanucleotides (spaced < or = 5 bases apart); (iii) direct and reverse repeats longer than 20 bp; and (iv) a number of motifs known from biochemical studies to play a role in the regulation of the BX-C [32].

Analytical, diagnostic and therapeutic context of Trinucleotides


  1. Protein-nucleotide interactions in E. coli DNA topoisomerase I. Feinberg, H., Changela, A., Mondragón, A. Nat. Struct. Biol. (1999) [Pubmed]
  2. Over- and under-representation of short oligonucleotides in DNA sequences. Burge, C., Campbell, A.M., Karlin, S. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  3. Erythroid pyrimidine 5'-nucleotidase: cloning, developmental expression, and regulation by cAMP and in vivo hypoxia. Mass, M., Simo, E., Dragon, S. Blood (2003) [Pubmed]
  4. Phosphorothioate di- and trinucleotides as a novel class of anti-hepatitis B virus agents. Iyer, R.P., Jin, Y., Roland, A., Morrey, J.D., Mounir, S., Korba, B. Antimicrob. Agents Chemother. (2004) [Pubmed]
  5. Expanded CTG triplet blocks from the myotonic dystrophy gene create the strongest known natural nucleosome positioning elements. Wang, Y.H., Griffith, J. Genomics (1995) [Pubmed]
  6. Huntington's disease and repeating trinucleotides. Gusella, J.F., MacDonald, M.E. N. Engl. J. Med. (1994) [Pubmed]
  7. Frequency analysis of large CAG/CTG trinucleotide repeats in schizophrenia and bipolar affective disorder. Vincent, J.B., Klempan, T., Parikh, S.S., Sasaki, T., Meltzer, H.Y., Sirugo, G., Cola, P., Petronis, A., Kennedy, J.L. Mol. Psychiatry (1996) [Pubmed]
  8. Clinical and genetic abnormalities in patients with Friedreich's ataxia. Dürr, A., Cossee, M., Agid, Y., Campuzano, V., Mignard, C., Penet, C., Mandel, J.L., Brice, A., Koenig, M. N. Engl. J. Med. (1996) [Pubmed]
  9. Length of uninterrupted CGG repeats determines instability in the FMR1 gene. Eichler, E.E., Holden, J.J., Popovich, B.W., Reiss, A.L., Snow, K., Thibodeau, S.N., Richards, C.S., Ward, P.A., Nelson, D.L. Nat. Genet. (1994) [Pubmed]
  10. Reversibility of cyclization of the Tetrahymena rRNA intervening sequence: implication for the mechanism of splice site choice. Sullivan, F.X., Cech, T.R. Cell (1985) [Pubmed]
  11. Control of CpNpG DNA methylation by the KRYPTONITE histone H3 methyltransferase. Jackson, J.P., Lindroth, A.M., Cao, X., Jacobsen, S.E. Nature (2002) [Pubmed]
  12. Sequence discrimination by alternatively spliced isoforms of a DNA binding zinc finger domain. Gogos, J.A., Hsu, T., Bolton, J., Kafatos, F.C. Science (1992) [Pubmed]
  13. Effect of interferon and 2',5'-oligoadenylates on rotavirus RNA synthesis. Ríos, M., Muñoz, M., Torrence, P.F., Spencer, E. Antiviral Res. (1995) [Pubmed]
  14. Historical review: Deciphering the genetic code--a personal account. Nirenberg, M. Trends Biochem. Sci. (2004) [Pubmed]
  15. Asymptotically increasing compliance of genomes with Chargaff's second parity rules through inversions and inverted transpositions. Albrecht-Buehler, G. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  16. An operational RNA code for amino acids and possible relationship to genetic code. Schimmel, P., Giegé, R., Moras, D., Yokoyama, S. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  17. Specific atomic groups and RNA helix geometry in acceptor stem recognition by a tRNA synthetase. Beuning, P.J., Yang, F., Schimmel, P., Musier-Forsyth, K. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  18. In vivo footprint and methylation analysis by PCR-aided genomic sequencing: comparison of active and inactive X chromosomal DNA at the CpG island and promoter of human PGK-1. Pfeifer, G.P., Tanguay, R.L., Steigerwald, S.D., Riggs, A.D. Genes Dev. (1990) [Pubmed]
  19. Strong cytosine-guanosine-independent immunostimulation in humans and other primates by synthetic oligodeoxynucleotides with PyNTTTTGT motifs. Elias, F., Flo, J., Lopez, R.A., Zorzopulos, J., Montaner, A., Rodriguez, J.M. J. Immunol. (2003) [Pubmed]
  20. The role of nucleotide pyrophosphatase in Mullerian duct regression. Fallat, M.E., Hutson, J.M., Budzik, G.P., Donahoe, P.K. Dev. Biol. (1983) [Pubmed]
  21. CpA containing oligoribonucleotides specifically inhibit protein synthesis in rabbit reticulocytes. Wagner, T., Gross, M., Sigler, P.B. FEBS Lett. (1987) [Pubmed]
  22. Inward rectification of the large conductance potassium channel in smooth muscle cells from rabbit pulmonary artery. Snetkov, V.A., Gurney, A.M., Ward, J.P., Osipenko, O.N. Exp. Physiol. (1996) [Pubmed]
  23. DNA methylation profiling identifies CG methylation clusters in Arabidopsis genes. Tran, R.K., Henikoff, J.G., Zilberman, D., Ditt, R.F., Jacobsen, S.E., Henikoff, S. Curr. Biol. (2005) [Pubmed]
  24. Mononucleotide and dinucleotide frequencies, and codon usage in poliovirion RNA. Rothberg, P.G., Wimmer, E. Nucleic Acids Res. (1981) [Pubmed]
  25. NTP pattern of avian embryonic red cells: role of RNA degradation and AMP deaminase/5'-nucleotidase activity. Baumann, R., Gotz, R., Dragon, S. Am. J. Physiol. Regul. Integr. Comp. Physiol. (2003) [Pubmed]
  26. Capillary electrophoretic study of carboplatin and analogues with nucleoside monophosphates, di- and trinucleotides. Küng, A., Zenker, A., Galanski, M., Keppler, B.K. J. Inorg. Biochem. (2001) [Pubmed]
  27. About a symmetry of the genetic code. Koch, A.J., Lehmann, J. J. Theor. Biol. (1997) [Pubmed]
  28. Depression in Parkinson's disease is related to a genetic polymorphism of the cannabinoid receptor gene (CNR1). Barrero, F.J., Ampuero, I., Morales, B., Vives, F., de Dios Luna Del Castillo, J., Hoenicka, J., García Yébenes, J. Pharmacogenomics J. (2005) [Pubmed]
  29. Primary mediastinal B-cell lymphoma: hypermutation of the BCL6 gene targets motifs different from those in diffuse large B-cell and follicular lymphomas. Malpeli, G., Barbi, S., Moore, P.S., Scardoni, M., Chilosi, M., Scarpa, A., Menestrina, F. Haematologica (2004) [Pubmed]
  30. Fully synthetic human combinatorial antibody libraries (HuCAL) based on modular consensus frameworks and CDRs randomized with trinucleotides. Knappik, A., Ge, L., Honegger, A., Pack, P., Fischer, M., Wellnhofer, G., Hoess, A., Wölle, J., Plückthun, A., Virnekäs, B. J. Mol. Biol. (2000) [Pubmed]
  31. Analysis of polyglutamine-coding repeats in the TATA-binding protein in different human populations and in patients with schizophrenia and bipolar affective disorder. Rubinsztein, D.C., Leggo, J., Crow, T.J., DeLisi, L.E., Walsh, C., Jain, S., Paykel, E.S. Am. J. Med. Genet. (1996) [Pubmed]
  32. Sequence analysis of the cis-regulatory regions of the bithorax complex of Drosophila. Lewis, E.B., Knafels, J.D., Mathog, D.R., Celniker, S.E. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  33. A "CAT" family of repetitive DNA sequences in Saccharomyces cerevisiae. Wildeman, A.G., Rasquinha, I., Nazar, R.N. J. Biol. Chem. (1986) [Pubmed]
  34. The effect of CAT trinucleotide interruptions on the age at onset of spinocerebellar ataxia type 1 (SCA1). Matsuyama, Z., Izumi, Y., Kameyama, M., Kawakami, H., Nakamura, S. J. Med. Genet. (1999) [Pubmed]
  35. Influence of terminal 3' phosphates or 2',3'-cyclic phosphates on the conformations of oligoriboadenylates, oligoribocytidylates, and the corresponding monomers. Markham, A.F., Uesugi, S., Ohtsuka, E., Ikehara, M. Biochemistry (1979) [Pubmed]
  36. Nuclease P1 digestion combined with tandem mass spectrometry for the structure determination of DNA photoproducts. Wang, Y., Taylor, J.S., Gross, M.L. Chem. Res. Toxicol. (1999) [Pubmed]
  37. Labelled trinucleotides as quantitative probes to identify Bacillus spp. using fluorescent in situ hybridization. Abella, C.A., Ivanov, V.N., Kim, I.S., Doncel, G.F. Mol. Cell. Probes (2000) [Pubmed]
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