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Chemical Compound Review

Adenosine 2'-phosphate     [(2R,3R,4R,5R)-2-(6- aminopurin-9-yl)-4...

Synonyms: CHEMBL57445, AG-A-94566, SureCN1417034, A9396_SIGMA, CHEBI:28223, ...
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Disease relevance of Adenosine 2'-phosphate


High impact information on Adenosine 2'-phosphate

  • In accordance with structural data, which show a bipartite binding mode of NADPH, substitution of Trp-676 does not affect 2'-AMP binding as seen by the inhibition of both wild-type CPR and the W676A mutant [2].
  • The molecular structure of RNase T1 is only marginally affected by 2'-AMP binding [3].
  • Analysis of retinal tissue incubated with 2':3'-cAMP shows only 2'-AMP as the reaction product, indicating the selective hydrolysis of the cyclic nucleotide [4].
  • Thus, 9 mM 2'-AMP inhibits NADPH-cytochrome c reductase to 10 to 20% of control activity while NADPH-supported oxidative demethyl ation and deformylation are essentially unchanged [5].
  • The very low rates of cleavage of beta-glycerophosphate and 2'-AMP ruled out any significant contribution of nonspecific phosphatase to the observed 5'-nucleotidase activity in myelin [6].

Biological context of Adenosine 2'-phosphate


Anatomical context of Adenosine 2'-phosphate


Associations of Adenosine 2'-phosphate with other chemical compounds

  • Most of this radiolabel was rendered acid-soluble by dilute alkaline digestion at 37 degrees C, yielding an approximately equal mixture of 2'-AMP and 3'-AMP, and by RNase digestion, identifying the acid-insoluble radioactive material as RNA [13].
  • The affinity of the enzyme for 2'-AMP, the inactivation by monoiodoacetic acid and the fluorescence intensity were examined [14].
  • The nucleotides studied were 5'-,3'-, and 2'-AMP, and 5'-CMP in the pH range 2 through 12 [15].
  • The affinity of the C560Y mutant enzyme to NADP+ decreased 9-fold compared to the wild-type enzyme, while the affinity to 2'-AMP was not significantly affected, suggesting that Cys560 is located in the nicotinamide binding site of the active, full-size enzyme in solution [16].
  • RNase U2, a purine-specific RNase, was specifically bound to this adsorbent at pH 4.5 and eluted critically at pH 5.9 in the presence of 1 M NaCl, corresponding to the pH dependence of the binding of 2'-AMP to RNase U2 [17].

Gene context of Adenosine 2'-phosphate

  • While the depression elicited by 5'-nucleotides was completely antagonized by the action of adenosine deaminase, AOPCP and 2'-AMP were only partially antagonized [18].
  • The modes of binding of adenosine 2'-monophosphate (2'-AMP) to the enzyme ribonuclease (RNase) T1 were determined by computer modelling studies [19].
  • 2-Chloroadenosine, which is resistant to the action of adenosine deaminase, was a more potent growth inhibitor, while 3'AMP and 2'-AMP, which are not hydrolyzed to adenosine by membrane 5'-nucleotidase, were ineffective [20].

Analytical, diagnostic and therapeutic context of Adenosine 2'-phosphate

  • The mutant enzyme, which shows reduced activity towards GpA and increased activity towards pGpC, pApC and pUpC compared with wild-type RNase T1, was co-crystallized with 2'-adenylic acid by microdialysis [8].
  • The 2'-AMP product was separated by cellulose thin-layer chromatography in 4 M MgSO4-0.5 M sodium acetate-2-propanol (80:18:2, v/v/v) [21].


  1. 31P NMR studies of the binding of adenosine-2'-phosphate to Lactobacillus casei dihydrofolate reductase. Birdsall, B., Roberts, G.C., Feeney, J., Burgen, A.S. FEBS Lett. (1977) [Pubmed]
  2. Engineering of a functional human NADH-dependent cytochrome P450 system. Döhr, O., Paine, M.J., Friedberg, T., Roberts, G.C., Wolf, C.R. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  3. Crystal structure of ribonuclease T1 complexed with adenosine 2'-monophosphate at 1.8-A resolution. Ding, J., Koellner, G., Grunert, H.P., Saenger, W. J. Biol. Chem. (1991) [Pubmed]
  4. Identification of 2':3'-cyclic nucleotide 3'-phosphodiesterase in the vertebrate retina. Giulian, D., Moore, S. J. Biol. Chem. (1980) [Pubmed]
  5. Mixed function oxidases in sterol metabolism. Separate routes for electron transfer from NADH and NADPH. Crowder, R.D., Brady, D.R. J. Biol. Chem. (1979) [Pubmed]
  6. 5'-nucleotidase in rat brain myelin. Cammer, W., Sirota, S.R., Zimmerman, T.R., Norton, W.T. J. Neurochem. (1980) [Pubmed]
  7. Effects of substrate and inhibitor binding on thermal and proteolytic inactivation of rat liver transhydrogenase. Blazyk, J.F., Lam, D. Biochemistry (1976) [Pubmed]
  8. Crystal structure of the Tyr45Trp mutant of ribonuclease T1 in a complex with 2'-adenylic acid. Koellner, G., Grunert, H.P., Landt, O., Saenger, W. Eur. J. Biochem. (1991) [Pubmed]
  9. Preference for syn conformation: crystal structures of free acid and ammonium salt of adenosine 2'-monophosphate: an inhibitor of RNase T1. Padiyar, G.S., Seshadri, T.P. J. Biomol. Struct. Dyn. (1998) [Pubmed]
  10. Poor myelination in the central nervous system of "dilute-lethal mutant mice" (d1/d1). Noguchi, T., Sugisaki, T., Tsukada, Y. Exp. Neurol. (1983) [Pubmed]
  11. An investigation of 2':3'-cyclic nucleotide 3'-phosphodiesterase (EC, CNP) in peripheral blood elements and CNS myelin. Sheedlo, H.J., Doran, J.E., Sprinkle, T.J. Life Sci. (1984) [Pubmed]
  12. Identification of 2',3'-cyclic nucleotide 3'-phosphodiesterase in bovine adrenal medulla. Tirrell, J.G., Coffee, C.J. Comp. Biochem. Physiol., B (1986) [Pubmed]
  13. NAD turnover and utilisation of metabolites for RNA synthesis in a reaction sensing the redox state of the cytochrome b6f complex in isolated chloroplasts. Pearson, C.K., Wilson, S.B., Schaffer, R., Ross, A.W. Eur. J. Biochem. (1993) [Pubmed]
  14. Characterization of Ustilago Ribonuclease U2. Effects of chemical modification at glutamic acid-61 and cystine-1 and of organic solvents on the enzymatic activity. Minato, S., Hirai, A. J. Biochem. (1979) [Pubmed]
  15. pH profile of the adsorption of nucleotides onto montmorillonite. I. Selected homoionic clays. Lawless, J.G., Banin, A., Church, F.M., Mazzurco, J., Huff, R., Kao, J., Cook, A., Lowe, T., Orenberg, J.B., Edelson, E. Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life. (1985) [Pubmed]
  16. Kinetic mechanism of cytochrome P450 reductase from the house fly (Musca domestica). Murataliev, M.B., Ariño, A., Guzov, V.M., Feyereisen, R. Insect Biochem. Mol. Biol. (1999) [Pubmed]
  17. An affinity adsorbent, 5'-adenylate-aminohexyl-sepharose. I. Purification and properties of two forms of RNase U2. Uchida, T., Shibata, Y. J. Biochem. (1981) [Pubmed]
  18. Effect of adenosine versus adenine nucleotides on evoked potentials in a rat hippocampal slice preparation. Lee, K.S., Schubert, P., Emmert, H., Kreutzberg, G.W. Neurosci. Lett. (1981) [Pubmed]
  19. Modes of binding of 2'-AMP to RNase T1. A computer modeling study. Balaji, P.V., Saenger, W., Rao, V.S. J. Biomol. Struct. Dyn. (1992) [Pubmed]
  20. Effect of adenosine and adenosine 5'-monophosphate on cell division of cultured mastocytoma P-815 cells. Ichikawa, A., Esumi, K., Takagi, M., Yatsunami, K., Negishi, M., Yokoyama, K., Tomita, K. J. Pharmacobio-dyn. (1980) [Pubmed]
  21. A method for chromatographic separation and fluorometric quantification of 2',3'-cyclic nucleotide-3'-phosphodiesterase reaction products. Pitkänen, A., Halonen, T.O., Kilpeläinen, H.O., Riekkinen, P.J. Anal. Biochem. (1984) [Pubmed]
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