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Chemical Compound Review

AG-J-04251     2-(6-aminopurin-9-yl)-5- methyl-oxolane-3,4...

Synonyms: D1771_SIGMA, NSC-86102, NSC-89222, SureCN12453581, CHEBI:120092, ...
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Disease relevance of CH3Ado


High impact information on CH3Ado


Chemical compound and disease context of CH3Ado


Biological context of CH3Ado

  • However, rather than simply binding inertly at the active site, 2-thiolglutarate elicits cobalt-carbon bond homolysis and the formation of 5'-deoxyadenosine [12].
  • The kinetics of deuterium incorporation into 5'-deoxyadenosine (5'-dA) during the reaction were followed by rapid chemical quench, using HPLC and electrospray mass spectrometry to analyze the 5'-dA formed [13].
  • These experiments also suggest that the presence of1in a duplex disrupts base pairing at the 5'-adjacent nucleotide and results in the thermally preferred misincorporation of purines opposite the 5'-deoxyadenosine stacked above 1 at this position [14].

Anatomical context of CH3Ado


Associations of CH3Ado with other chemical compounds


Gene context of CH3Ado

  • All the compounds except 5'-deoxyadenosine, however, also caused the undesirable rescue of MTAP-negative ATL cell lines [15].
  • However, in the presence of 5-10 microM of 5'-deoxyadenosine, colony formation of hematopoietic stem/primitive progenitors was restored [10].
  • However, all computed activation enthalpies exceed the experimentally derived activation enthalpy (15 kcal/mol) associated with the rate-determining step, i.e., the hydrogen abstraction from the 5'-deoxyadenosine by the product radical [18].

Analytical, diagnostic and therapeutic context of CH3Ado


  1. Transport of a nonphosphorylated nucleoside, 5'-deoxyadenosine, by murine leukemia L1210 cells. Kessel, D. J. Biol. Chem. (1978) [Pubmed]
  2. Interaction of 3'-[3H]2'-Chloro-2'-deoxyuridine 5'-triphosphate with ribonucleotide reductase from Lactobacillus leichmannii. Stubbe, J., Smith, G., Blakley, R.L. J. Biol. Chem. (1983) [Pubmed]
  3. Reaction of 5'-deoxyadenosine and related analogs with the 5'-methylthioadenosine cleaving enzyme of sarcoma 180 cells, a possible chemotherapeutic target enzyme. Savarese, T.M., Crabtree, G.W., Parks, R.E. Biochem. Pharmacol. (1979) [Pubmed]
  4. Adenine nucleosides in solution: circular dichroism studies and base conformation. Follmann, H., Kuntz, I., Zacharias, W. Eur. J. Biochem. (1975) [Pubmed]
  5. Derivatives of 3'- and 5'-deoxyadenosine: their inhibitory activity against DNA viruses. Grytzmann, B., Morr, M., Wigand, R. Chemotherapy. (1980) [Pubmed]
  6. Biochemistry of coenzyme B12-dependent glycerol and diol dehydratases and organization of the encoding genes. Daniel, R., Bobik, T.A., Gottschalk, G. FEMS Microbiol. Rev. (1998) [Pubmed]
  7. Characterization of an active spore photoproduct lyase, a DNA repair enzyme in the radical S-adenosylmethionine superfamily. Buis, J.M., Cheek, J., Kalliri, E., Broderick, J.B. J. Biol. Chem. (2006) [Pubmed]
  8. Adenosylmethionine-dependent synthesis of the glycyl radical in pyruvate formate-lyase by abstraction of the glycine C-2 pro-S hydrogen atom. Studies of [2H]glycine-substituted enzyme and peptides homologous to the glycine 734 site. Frey, M., Rothe, M., Wagner, A.F., Knappe, J. J. Biol. Chem. (1994) [Pubmed]
  9. The mechanism of action of ethanolamine ammonia-lyase, an adenosylcobalamin-dependent enzyme. The source of the third methyl hydrogen in the 5'-deoxyadenosine generated from the cofactor during catalysis. Sato, K., Orr, J.C., Babior, B.M., Abeles, R.H. J. Biol. Chem. (1976) [Pubmed]
  10. Presence of methylthioadenosine phosphorylase (MTAP) in hematopoietic stem/progenitor cells: its therapeutic implication for MTAP (-) malignancies. Yu, J., Batova, A., Shao, L., Carrera, C.J., Yu, A.L. Clin. Cancer Res. (1997) [Pubmed]
  11. 5'-Methylthioadenosine phosphorylase-L. Substrate activity of 5'-deoxyadenosine with the enzyme from Sarcoma 180 cells. Savarese, T.M., Crabtree, G.W., Parks, R.E. Biochem. Pharmacol. (1981) [Pubmed]
  12. Reaction of adenosylcobalamin-dependent glutamate mutase with 2-thiolglutarate. Yoon, M., Patwardhan, A., Qiao, C., Mansoorabadi, S.O., Menefee, A.L., Reed, G.H., Marsh, E.N. Biochemistry (2006) [Pubmed]
  13. Isotope effects for deuterium transfer between substrate and coenzyme in adenosylcobalamin-dependent glutamate mutase. Cheng, M.C., Marsh, E.N. Biochemistry (2005) [Pubmed]
  14. The effects of 5R-5,6-dihydro-5-hydroxythymidine on duplex DNA stability and structure. Sambandam, A., Greenberg, M.M. Nucleic Acids Res. (1999) [Pubmed]
  15. Chemotherapy targeting methylthioadenosine phosphorylase (MTAP) deficiency in adult T cell leukemia (ATL). Harasawa, H., Yamada, Y., Kudoh, M., Sugahara, K., Soda, H., Hirakata, Y., Sasaki, H., Ikeda, S., Matsuo, T., Tomonaga, M., Nobori, T., Kamihira, S. Leukemia (2002) [Pubmed]
  16. Hydrogen atom exchange between 5'-deoxyadenosine and hydroxyethylhydrazine during the single turnover inactivation of ethanolamine ammonia-lyase. Bandarian, V., Poyner, R.R., Reed, G.H. Biochemistry (1999) [Pubmed]
  17. Adenosine metabolism in wild-type and enzyme-deficient variants of Chinese hamster ovary and Novikoff rat hepatoma cells. Plagemann, P.G., Wohlhueter, R.M. J. Cell. Physiol. (1983) [Pubmed]
  18. Computational study on mechanistic details of the aminoethanol rearrangement catalyzed by the vitamin B12-dependent ethanolamine ammonia lyase: His and Asp/Glu acting simultaneously as catalytic auxiliaries. Semialjac, M., Schwarz, H. J. Org. Chem. (2003) [Pubmed]
  19. The subunit structure and catalytic mechanism of the Bacillus subtilis DNA repair enzyme spore photoproduct lyase. Rebeil, R., Nicholson, W.L. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
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