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Chemical Compound Review

AG-F-54429     (2R,3R,4S,5R)-2-(6-amino-8- azido-purin-9...

Synonyms: AC1Q1UDI, KB-46644, CTK1D6840, ZINC13515580, AR-1H4371, ...
 
 
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Disease relevance of Adenosine, 8-azido-

  • We have recently demonstrated that two ATP analog affinity labels, 8-azidoadenosine 5'-triphosphate (N3ATP) and 5'-p-fluorosulfonylbenzoyladenosine (5'FSBA), covalently modify RecA protein of Escherichia coli at a specific tyrosine residue (Tyr-264) located within a 24-residue tryptic peptide (T-31) spanning residues 257-280 [1].
  • We have used 8-azidoadenosine 5'-triphosphate (8-N3ATP) to investigate the nucleotide-binding sites on the NrdD subunit of the anaerobic ribonucleotide reductase from T4 phage [2].
  • We have used the photoaffinity analogs 8-azidoadenosine 5'-triphosphate (8-N3ATP) and 8-azidoguanosine 5'-triphosphate (8-N3GTP) to investigate the relationship between a viral induced protein (Mr = 120,000) in tobacco mosaic virus (TMV)-infected tobacco and the TMV-induced RNA-dependent RNA polymerase activity [3].
  • However, its true potential as a photoactivatable nucleotide analog could not be exploited due to the lack of 8-azidoadenosine phosphoramidite, a monomer used in the synthesis of RNA, and the inability of 8-N(3)ATP to serve as an efficient substrate for bacteriophage RNA polymerase [4].
  • Bacillus subtilis glutamine synthetase was modified by two ATP analogs, 5'-p-fluorosulfonylbenzoyladenosine (FSBA) and 8-azidoadenosine 5'-triphosphate (8-N3-ATP), each one containing either Mg2+ or Mn2+ [5].
 

High impact information on Adenosine, 8-azido-

  • RI and both forms of RII were covalently labeled with 8-azidoadenosine 3',5'-cyclic [32P]monophosphate, and two anti-RII antibodies that exclusively recognize either RII52 or RII56 resolved two forms of the RII receptors [6].
  • We examined the interactions between CFTR and nucleotides using 8-azidoadenosine 5'-triphosphate (8-N3-ATP), a photoactivatable ATP analog [7].
  • Tyrosine 65 is photolabeled by 8-azidoadenine and 8-azidoadenosine at the NAD binding site of diphtheria toxin [8].
  • 8-Azidoadenosine 5'-triphosphate [( alpha-32P]8-N3ATP) has been used to photolabel the ATP-binding site in yeast glutamine synthetase [9].
  • Pre-treatment of cells with colchicine or 8-azidoadenosine 3',5'-cyclic phosphate, but not lumicolchicine, resulted in reduction of the t1/2 for DAF to 1 to 2.6 min [10].
 

Chemical compound and disease context of Adenosine, 8-azido-

 

Biological context of Adenosine, 8-azido-

  • We have used 8-azidoadenosine 5'-triphosphate (8-N3ATP), a photoaffinity analog of ATP, to investigate which of the dynein polypeptides contains the site of ATP hydrolysis [13].
  • Identification of amino acid residues photolabeled with 8-azidoadenosine 5'-diphosphate in the catalytic site of sarcoplasmic reticulum Ca-ATPase [14].
  • In the presence of ultraviolet light, 8-azidoadenosine 5'-monophosphate is irreversibly incorporated into phosphorylase a; incorporation at the allosteric site can be reduced if AMP is added prior to irradiation [15].
  • The present results indicate that 8-azidoadenosine 5'-monophosphate is kinetically specific for the catalytic NAD(H)-binding site, but reacts covalently with Tyr 1006 of the putative non-catalytic site or nicotinamide nucleotide-binding domain formed by the 1001-1027 amino acid sequence of the catalytic NADP(H)-binding site [16].
 

Anatomical context of Adenosine, 8-azido-

 

Associations of Adenosine, 8-azido- with other chemical compounds

 

Gene context of Adenosine, 8-azido-

 

Analytical, diagnostic and therapeutic context of Adenosine, 8-azido-

  • The incorporation of 8N3A into tRNA(Phe) was accomplished by ligation of 8-azidoadenosine 3',5'-bisphosphate to the 3' end of tRNA molecules which were shortened by either one or four nucleotides [20].

References

  1. Nucleotide binding by a 24-residue peptide from the RecA protein of Escherichia coli. Knight, K.L., McEntee, K. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  2. Localization and characterization of two nucleotide-binding sites on the anaerobic ribonucleotide reductase from bacteriophage T4. Olcott, M.C., Andersson, J., Sjöberg, B.M. J. Biol. Chem. (1998) [Pubmed]
  3. Photoaffinity labeling of a viral induced protein from tobacco. Characterization of nucleotide-binding properties. Evans, R.K., Haley, B.E., Roth, D.A. J. Biol. Chem. (1985) [Pubmed]
  4. Template-dependent incorporation of 8-N3AMP into RNA with bacteriophage T7 RNA polymerase. Gopalakrishna, S., Gusti, V., Nair, S., Sahar, S., Gaur, R.K. RNA (2004) [Pubmed]
  5. Identification of amino acid residues modified by two ATP analogs in Bacillus subtilis glutamine synthetase. Tanaka, E., Kimura, K. J. Biochem. (1991) [Pubmed]
  6. Selective modulation of protein kinase isozymes by the site-selective analog 8-chloroadenosine 3',5'-cyclic monophosphate provides a biological means for control of human colon cancer cell growth. Ally, S., Tortora, G., Clair, T., Grieco, D., Merlo, G., Katsaros, D., Ogreid, D., Døskeland, S.O., Jahnsen, T., Cho-Chung, Y.S. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  7. Interaction of nucleotides with membrane-associated cystic fibrosis transmembrane conductance regulator. Travis, S.M., Carson, M.R., Ries, D.R., Welsh, M.J. J. Biol. Chem. (1993) [Pubmed]
  8. Tyrosine 65 is photolabeled by 8-azidoadenine and 8-azidoadenosine at the NAD binding site of diphtheria toxin. Papini, E., Santucci, A., Schiavo, G., Domenighini, M., Neri, P., Rappuoli, R., Montecucco, C. J. Biol. Chem. (1991) [Pubmed]
  9. Sequence of peptides from Saccharomyces cerevisiae glutamine synthetase. N-terminal peptide and ATP-binding domain. Kim, K.H., Rhee, S.G. J. Biol. Chem. (1988) [Pubmed]
  10. Association of cytoskeletal re-organization with capping of the complement decay-accelerating factor on T lymphocytes. Kammer, G.M., Walter, E.I., Medof, M.E. J. Immunol. (1988) [Pubmed]
  11. Azidopolynucleotides as photoaffinity reagents. Cartwright, I.L., Hutchinson, D.W. Nucleic Acids Res. (1980) [Pubmed]
  12. Probing tRNA binding sites on the Escherichia coli 30 S ribosomal subunit with photoreactive analogs of the anticodon arm. Wower, J., Malloy, T.A., Hixson, S.S., Zimmermann, R.A. Biochim. Biophys. Acta (1990) [Pubmed]
  13. The photoaffinity probe 8-azidoadenosine 5'-triphosphate selectively labels the heavy chain of Chlamydomonas 12 S dynein. Pfister, K.K., Haley, B.E., Witman, G.B. J. Biol. Chem. (1984) [Pubmed]
  14. Identification of amino acid residues photolabeled with 8-azidoadenosine 5'-diphosphate in the catalytic site of sarcoplasmic reticulum Ca-ATPase. Lacapère, J.J., Garin, J., Trinnaman, B., Green, N.M. Biochemistry (1993) [Pubmed]
  15. Interaction of glycogen phosphorylase with 8-azidoadenosine 5'-monophosphate, a photoaffinity analog of AMP. Seery, V.L. Biochim. Biophys. Acta (1980) [Pubmed]
  16. Energy-linked transhydrogenase. Characterization of a nucleotide-binding sequence in nicotinamide nucleotide transhydrogenase from beef heart. Hu, P.S., Persson, B., Höög, J.O., Jörnvall, H., Hartog, A.F., Berden, J.A., Holmberg, E., Rydström, J. Biochim. Biophys. Acta (1992) [Pubmed]
  17. Photoaffinity labeling of the human erythrocyte glucose transporter with 8-azidoadenosine. Jarvis, S.M., Young, J.D., Wu, J.S., Belt, J.A., Paterson, A.R. J. Biol. Chem. (1986) [Pubmed]
  18. Identification, characterization, and quantitative measurement of cyclic AMP receptor proteins in cytosol of various tissues using a photoaffinity ligand. Walter, U., Uno, I., Liu, A.Y., Greengard, P. J. Biol. Chem. (1977) [Pubmed]
  19. Photoaffinity labeling of adenosine 3',5'-cyclic monophosphate binding sites of human red cell membranes. Haley, B.E. Biochemistry (1975) [Pubmed]
  20. Photochemical cross-linking of yeast tRNA(Phe) containing 8-azidoadenosine at positions 73 and 76 to the Escherichia coli ribosome. Wower, J., Hixson, S.S., Zimmermann, R.A. Biochemistry (1988) [Pubmed]
  21. Photoaffinity labeling of the nucleotide binding site of actin. Hegyi, G., Szilagyi, L., Elzinga, M. Biochemistry (1986) [Pubmed]
  22. Photoaffinity labeling with 8-azidoadenosine and its derivatives: chemistry of closed and opened adenosine diazaquinodimethanes. Polshakov, D., Rai, S., Wilson, R.M., Mack, E.T., Vogel, M., Krause, J.A., Burdzinski, G., Platz, M.S. Biochemistry (2005) [Pubmed]
  23. Biochemistry of terminal deoxynucleotidyltransferase: characterization and properties of photoaffinity labeling with 8-azidoadenosine 5'-triphosphate. Abraham, K.I., Haley, B., Modak, M.J. Biochemistry (1983) [Pubmed]
  24. The topology of the glutamine and ATP binding sites of human asparagine synthetase. Larsen, M.C., Schuster, S.M. Arch. Biochem. Biophys. (1992) [Pubmed]
  25. Identification and characterization of a nucleotide binding site on recombinant murine granulocyte/macrophage-colony stimulating factor. Doukas, M.A., Chavan, A.J., Gass, C., Boone, T., Haley, B.E. Bioconjug. Chem. (1992) [Pubmed]
  26. Synthesis, characterization, and biological properties of 8-azido- and 8-amino-substituted 2',5'-oligoadenylates. Sawai, H., Hirano, A., Mori, H., Shinozuka, K., Dong, B., Silverman, R.H. J. Med. Chem. (2003) [Pubmed]
  27. Photochemical labeling of bovine pancreatic ribonuclease A with 8-azidoadenosine 3',5'-bisphosphate. Wower, J., Aymie, M., Hixson, S.S., Zimmermann, R.A. Biochemistry (1989) [Pubmed]
  28. Photoaffinity labeling of the adenosine cyclic 3',5'-monophosphate receptor protein of Escherichia coli with 8-azidoadenosine 3',5'-monophosphate. Aiba, H., Krakow, J.S. Biochemistry (1980) [Pubmed]
 
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