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Chemical Compound Review

Phosphonate     dioxido-oxo-phosphanium

Synonyms: AG-G-14933, CHEBI:16215, CHEBI:30932, PHO3(2-), CTK5B1013, ...
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Disease relevance of dioxido-oxo-phosphonium


High impact information on dioxido-oxo-phosphonium

  • Members of the other family, called the integrase family, contain a conserved tyrosine residue that forms a covalent linkage with the 3'-phosphate of DNA at the site of recombination [6].
  • We show that polynucleotide kinase (PNK), with its ability to process ionizing radiation-induced 5'-OH and 3'-phosphate DNA termini, functions in NHEJ via an FHA-dependent interaction with CK2-phosphorylated Xrcc4 [7].
  • The substrate, anchored through the 3'-phosphate ADP moiety, allows the fatty acid tail to pivot from the ECH to HACD active sites, and finally to the KACT active site [8].
  • Slalom encodes an adenosine 3'-phosphate 5'-phosphosulfate transporter essential for development in Drosophila [9].
  • Here we report the first molecular identification of a gene that encodes a transmembrane protein required to transport adenosine 3'-phosphate 5'-phosphosulfate from the cytosol into the Golgi lumen [9].

Chemical compound and disease context of dioxido-oxo-phosphonium


Biological context of dioxido-oxo-phosphonium

  • The mechanism of 3'-phosphate cyclization was studied with oligoribonucleotides containing terminal 2'-deoxy- or 2'-O-methylribose [14].
  • Synthetic polynucleotides terminated by a 3'-phosphate are resistant to hydrolysis [15].
  • Human polydeoxyribonucleotide kinase is an enzyme that has the capacity to phosphorylate DNA at 5'-hydroxyl termini and dephosphorylate 3'-phosphate termini and, therefore, can be considered a putative DNA repair enzyme [16].
  • The endonucleolytic activity of the tRNA-splicing system in the HeLa extract produces exons with 3'-phosphate and 5'-hydroxyl groups [17].
  • Nucleotide sequence analysis of the eight cleavage products has shown that the enzyme produces oligonucleotides terminating in 3'-phosphate groups, and that the four cleavage sites are in the only nonhydrogen-bonded region of the substrate [18].

Anatomical context of dioxido-oxo-phosphonium


Associations of dioxido-oxo-phosphonium with other chemical compounds

  • The AMP group is then transferred to the 3'-phosphate in RNA, yielding an RNA-N(3')pp(5')A (N is any nucleoside) intermediate, which finally undergoes cyclization [24].
  • It shows a new mode of nucleotide binding at the active site with the 3'-phosphate of PAPS located near the catalytic histidine, at the same position as the gamma-phosphate in the transition state [25].
  • We have used isothermal titration calorimetry to quantify the effects of varying acyl chain length and removing the 3'-phosphate group of CoA on the energetics of interaction between Nmt1p and acyl-CoA ligands [26].
  • At 30 degrees C, pH 8.0 (0.1 M Tris-chloride buffer), 5.5 microM APS, 5 mM MgATP, 5 mM excess MgCl2, and "high" salt (70-150 mM (NH4)2SO4), the most highly purified preparation has a specific activity of 24.7 units X mg of protein-1 in the physiological direction of adenosine 3'-phosphate 5'-phosphosulfate (PAPS) formation [27].
  • Galactosylceramide sulfotransferase (EC catalyzes the biosynthesis of sulfatide from galactocerebroside and adenosine 3'-phosphate 5'-phosphosulfate (PAPS) [28].

Gene context of dioxido-oxo-phosphonium

  • Tyrosyl DNA phosphodiesterase 1 (TDP1) is a repair enzyme that removes adducts, e.g. of topoisomerase I from the 3'-phosphate of DNA breaks [29].
  • The source of these phosphates remains enigmatic, however, because apn1 tpp1 rad1 slow growth could be correlated with neither the presence of a yeast delta-lyase, the activity of the 3'-phosphate-generating enzyme Tdp1, nor levels of endogenous oxidation [30].
  • PNKP gene function restored termini suitable for DNA polymerase, consistent with in vivo removal of 3'-phosphate groups, facilitating DNA repair [31].
  • Although Arg130 is also located very close to the 3'-phosphate of PAPS, R130A and R130E are still active, suggesting that Arg130 is not a critical residue for the catalytic activity of SULT1A1 [32].
  • One of these is activation of phosphatidylinositol 3-kinase (PI-3K), which results in the generation of a membrane-restricted second messenger, polyphosphatidylinositides containing a 3'-phosphate [33].

Analytical, diagnostic and therapeutic context of dioxido-oxo-phosphonium

  • Removal of the 3'-phosphate from the 5' half eliminates the ability of the 5' half to participate in ligation [34].
  • After removing 3'-phosphate for better recognition by the antibodies, the resulting alkyl nucleotides were further fractionated by HPLC and finally precipitated specifically with respective antibodies [35].
  • Substitution of 3'-phosphate cap with a carbon-based blocker reduces the possibility of fluorescence resonance energy transfer probe failure in real-time PCR assays [36].
  • The 16 structurally identified benzo[c]phenanthrene-purine deoxyribonucleoside 3'-phosphate adducts were then separately postlabeled according to the Randerath method, and the positions of the individual bisphosphates were mapped by thin-layer chromatography [37].
  • Synthesis and 32P-postlabeling/high-performance liquid chromatography separation of diastereomeric 1,N2-(1,3-propano)-2'-deoxyguanosine 3'-phosphate adducts formed from 4-hydroxy-2-nonenal [38].


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  3. Polyribosome binding of rabbit globin messenger RNA and messenger ribonucleoprotein labelled with bacteriophage-T4 RNA ligase and 5'-[32P] phosphocytidine 3'-phosphate. Thomas, N.S., Butcher, P.D., Arnstein, H.R. Nucleic Acids Res. (1983) [Pubmed]
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  6. A protein binding to the J kappa recombination sequence of immunoglobulin genes contains a sequence related to the integrase motif. Matsunami, N., Hamaguchi, Y., Yamamoto, Y., Kuze, K., Kangawa, K., Matsuo, H., Kawaichi, M., Honjo, T. Nature (1989) [Pubmed]
  7. Xrcc4 physically links DNA end processing by polynucleotide kinase to DNA ligation by DNA ligase IV. Koch, C.A., Agyei, R., Galicia, S., Metalnikov, P., O'Donnell, P., Starostine, A., Weinfeld, M., Durocher, D. EMBO J. (2004) [Pubmed]
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  9. Slalom encodes an adenosine 3'-phosphate 5'-phosphosulfate transporter essential for development in Drosophila. Lüders, F., Segawa, H., Stein, D., Selva, E.M., Perrimon, N., Turco, S.J., Häcker, U. EMBO J. (2003) [Pubmed]
  10. Allosteric interactions coordinate catalytic activity between successive metabolic enzymes in the tryptophan synthase bienzyme complex. Brzović, P.S., Ngo, K., Dunn, M.F. Biochemistry (1992) [Pubmed]
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  12. Inactivation of kanamycin A by phosphorylation in pathogenic Nocardia. Yazawa, K., Mikami, Y., Maeda, A., Kudo, T., Suzuki, K., Saito, N., Kubo, A. Microbiol. Immunol. (1991) [Pubmed]
  13. Extracellular ATP has stimulatory effects on the expression and release of IL-6 via purinergic receptors in normal human epidermal keratinocytes. Inoue, K., Hosoi, J., Denda, M. J. Invest. Dermatol. (2007) [Pubmed]
  14. Cyclization of RNA 3'-terminal phosphate by cyclase from HeLa cells proceeds via formation of N(3')pp(5')A activated intermediate. Filipowicz, W., Strugala, K., Konarska, M., Shatkin, A.J. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  15. A guanosine 3':5'-monophosphate-sensitive nuclease from Bacillus brevis. Sarkar, N., Paulus, H. J. Biol. Chem. (1975) [Pubmed]
  16. Molecular characterization of a human DNA kinase. Karimi-Busheri, F., Daly, G., Robins, P., Canas, B., Pappin, D.J., Sgouros, J., Miller, G.G., Fakhrai, H., Davis, E.M., Le Beau, M.M., Weinfeld, M. J. Biol. Chem. (1999) [Pubmed]
  17. Characterization of tRNA precursor splicing in mammalian extracts. Laski, F.A., Fire, A.Z., RajBhandary, U.L., Sharp, P.A. J. Biol. Chem. (1983) [Pubmed]
  18. Characterization of ribonuclease NU cleavage sites in a bacteriophage phi80-induced ribonucleic acid. Bothwell, A.L., Altman, S. J. Biol. Chem. (1975) [Pubmed]
  19. Enzymatic sulfation of exogenous high molecular weight glycopeptides by microsomal fraction of the rabbit uterine endometrium. Munakata, H., Isemura, M., Yosizawa, Z. J. Biol. Chem. (1985) [Pubmed]
  20. Direct photoaffinity labeling of proteins with adenosine 3'-[32P]phosphate 5'-phosphosulfate. Atractyloside inhibits labeling of a Mr = 34,000 protein in an adrenal medullary Golgi fraction. Lee, R.W., Suchanek, C., Huttner, W.B. J. Biol. Chem. (1984) [Pubmed]
  21. Cystic fibrosis transmembrane conductance regulator-associated ATP and adenosine 3'-phosphate 5'-phosphosulfate channels in endoplasmic reticulum and plasma membranes. Pasyk, E.A., Foskett, J.K. J. Biol. Chem. (1997) [Pubmed]
  22. Characterization of a sulfotransferase from human airways responsible for the 3-O-sulfation of terminal galactose in N-acetyllactosamine-containing mucin carbohydrate chains. Lo-Guidice, J.M., Périni, J.M., Lafitte, J.J., Ducourouble, M.P., Roussel, P., Lamblin, G. J. Biol. Chem. (1995) [Pubmed]
  23. RNA 3'-terminal phosphate cyclase activity and RNA ligation in HeLa cell extract. Filipowicz, W., Konarska, M., Gross, H.J., Shatkin, A.J. Nucleic Acids Res. (1983) [Pubmed]
  24. Characterization of the adenylation site in the RNA 3'-terminal phosphate cyclase from Escherichia coli. Billy, E., Hess, D., Hofsteenge, J., Filipowicz, W. J. Biol. Chem. (1999) [Pubmed]
  25. 3'-Phosphorylated nucleotides are tight binding inhibitors of nucleoside diphosphate kinase activity. Schneider, B., Xu, Y.W., Janin, J., Véron, M., Deville-Bonne, D. J. Biol. Chem. (1998) [Pubmed]
  26. Isothermal titration calorimetric studies of Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase. Determinants of binding energy and catalytic discrimination among acyl-CoA and peptide ligands. Bhatnagar, R.S., Jackson-Machelski, E., McWherter, C.A., Gordon, J.I. J. Biol. Chem. (1994) [Pubmed]
  27. Adenosine 5'-phosphosulfate kinase from Penicillium chrysogenum. Purification and kinetic characterization. Renosto, F., Seubert, P.A., Segel, I.H. J. Biol. Chem. (1984) [Pubmed]
  28. Purification and activation of brain sulfotransferase. Sundaram, K.S., Lev, M. J. Biol. Chem. (1992) [Pubmed]
  29. TDP1 overexpression in human cells counteracts DNA damage mediated by topoisomerases I and II. Barthelmes, H.U., Habermeyer, M., Christensen, M.O., Mielke, C., Interthal, H., Pouliot, J.J., Boege, F., Marko, D. J. Biol. Chem. (2004) [Pubmed]
  30. The role of yeast DNA 3'-phosphatase Tpp1 and rad1/Rad10 endonuclease in processing spontaneous and induced base lesions. Karumbati, A.S., Deshpande, R.A., Jilani, A., Vance, J.R., Ramotar, D., Wilson, T.E. J. Biol. Chem. (2003) [Pubmed]
  31. Molecular cloning of the human gene, PNKP, encoding a polynucleotide kinase 3'-phosphatase and evidence for its role in repair of DNA strand breaks caused by oxidative damage. Jilani, A., Ramotar, D., Slack, C., Ong, C., Yang, X.M., Scherer, S.W., Lasko, D.D. J. Biol. Chem. (1999) [Pubmed]
  32. Arginine residues in the active site of human phenol sulfotransferase (SULT1A1). Chen, G., Chen, X. J. Biol. Chem. (2003) [Pubmed]
  33. Protein kinase B (c-Akt): a multifunctional mediator of phosphatidylinositol 3-kinase activation. Coffer, P.J., Jin, J., Woodgett, J.R. Biochem. J. (1998) [Pubmed]
  34. Splicing of yeast tRNA precursors: structure of the reaction intermediates. Knapp, G., Ogden, R.C., Peebles, C.L., Abelson, J. Cell (1979) [Pubmed]
  35. Highly sensitive, specific detection of O6-methylguanine, O4-methylthymine, and O4-ethylthymine by the combination of high-performance liquid chromatography prefractionation, 32P postlabeling, and immunoprecipitation. Kang, H.I., Konishi, C., Eberle, G., Rajewsky, M.F., Kuroki, T., Huh, N.H. Cancer Res. (1992) [Pubmed]
  36. Substitution of 3'-phosphate cap with a carbon-based blocker reduces the possibility of fluorescence resonance energy transfer probe failure in real-time PCR assays. Cradic, K.W., Wells, J.E., Allen, L., Kruckeberg, K.E., Singh, R.J., Grebe, S.K. Clin. Chem. (2004) [Pubmed]
  37. Identification of individual benzo[c]phenanthrene dihydrodiol epoxide-DNA adducts by the 32P-postlabeling assay. Canella, K.A., Peltonen, K., Yagi, H., Jerina, D.M., Dipple, A. Chem. Res. Toxicol. (1992) [Pubmed]
  38. Synthesis and 32P-postlabeling/high-performance liquid chromatography separation of diastereomeric 1,N2-(1,3-propano)-2'-deoxyguanosine 3'-phosphate adducts formed from 4-hydroxy-2-nonenal. Yi, P., Zhan, D., Samokyszyn, V.M., Doerge, D.R., Fu, P.P. Chem. Res. Toxicol. (1997) [Pubmed]
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