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Chemical Compound Review

CHEMBL1094973     [[[(2R,3S,4R,5R)-5-(2-amino- 7-methyl-6-oxo...

Synonyms: CHEBI:50210, m(7)GTP, CHEBI:724254, AIDS166754, AC1LD926, ...
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High impact information on 7-METHYL-GUANOSINE-5'-TRIPHOSPHATE


Biological context of 7-METHYL-GUANOSINE-5'-TRIPHOSPHATE


Anatomical context of 7-METHYL-GUANOSINE-5'-TRIPHOSPHATE


Associations of 7-METHYL-GUANOSINE-5'-TRIPHOSPHATE with other chemical compounds



  • The association constant values of recombinant eIF4E for 20 different cap analogues cover six orders of magnitude; with the highest affinity observed for m(7)GTP (approximately 1.1 x 10(8) M(-1)) [11].
  • Alternatively cell lysates were exposed to 7-methyl GTP Sepharose beads in order to isolate the cap-binding protein eIF-4E [12].
  • This was confirmed further by 7-methyl-GTP Sepharose isolation of eIF-4E with which 4E-BP1 coprecipitates [12].
  • The cap analogue m(7)GTP, but not GTP, inhibited VPg-eIF(iso)4E complex formation, suggesting that VPg and cellular mRNAs compete for eIF(iso)4E binding [13].
  • Eukaryotic translation initiation factor 4E (eIF4E) binds to the m(7)GTP of capped mRNAs and is an essential component of the translational machinery that recruits the 40S small ribosomal subunit [14].

Analytical, diagnostic and therapeutic context of 7-METHYL-GUANOSINE-5'-TRIPHOSPHATE

  • High-pressure liquid chromatography analysis confirmed the production of m(7)GTP by the GTP methyltransferase activity of H68A [15].
  • Fluorescence titration experiments with eIF4E and the nuclear cap-binding complex CBC indicated affinities for RTP and RpppG that were two to four orders of magnitude lower than those of m(7)GTP and m(7)GpppG [16].


  1. Raptor, a binding partner of target of rapamycin (TOR), mediates TOR action. Hara, K., Maruki, Y., Long, X., Yoshino, K., Oshiro, N., Hidayat, S., Tokunaga, C., Avruch, J., Yonezawa, K. Cell (2002) [Pubmed]
  2. Inhibition of cap-dependent translation via phosphorylation of eIF4G by protein kinase Pak2. Ling, J., Morley, S.J., Traugh, J.A. EMBO J. (2005) [Pubmed]
  3. Cap-dependent deadenylation of mRNA. Dehlin, E., Wormington, M., Körner, C.G., Wahle, E. EMBO J. (2000) [Pubmed]
  4. Two zebrafish eIF4E family members are differentially expressed and functionally divergent. Robalino, J., Joshi, B., Fahrenkrug, S.C., Jagus, R. J. Biol. Chem. (2004) [Pubmed]
  5. Regulation of mRNA entry into polysomes. Parameters affecting polysome size and the fraction of mRNA in polysomes. Nelson, E.M., Winkler, M.M. J. Biol. Chem. (1987) [Pubmed]
  6. Internal entry of ribosomes on a tricistronic mRNA encoded by infectious bronchitis virus. Liu, D.X., Inglis, S.C. J. Virol. (1992) [Pubmed]
  7. Virus-specific mRNA capping enzyme encoded by hepatitis E virus. Magden, J., Takeda, N., Li, T., Auvinen, P., Ahola, T., Miyamura, T., Merits, A., Kääriäinen, L. J. Virol. (2001) [Pubmed]
  8. Quantitative analysis of influenza virus RNP interaction with RNA cap structures and comparison to human cap binding protein eIF4E. Hooker, L., Sully, R., Handa, B., Ono, N., Koyano, H., Klumpp, K. Biochemistry (2003) [Pubmed]
  9. Inhibitory effects of 'cap' analogues on globin mRNA and encephalomyocarditis RNA translation in a reticulocyte cell-free system. Fresno, M., Vázquez, D. Eur. J. Biochem. (1980) [Pubmed]
  10. Phenyl azide substituted and benzophenone-substituted phosphonamides of 7-methylguanosine 5'-triphosphate as photoaffinity probes for protein synthesis initiation factor eIF-4E and a proteolytic fragment containing the cap-binding site. Chavan, A.J., Rychlik, W., Blaas, D., Kuechler, E., Watt, D.S., Rhoads, R.E. Biochemistry (1990) [Pubmed]
  11. Biophysical studies of eIF4E cap-binding protein: recognition of mRNA 5' cap structure and synthetic fragments of eIF4G and 4E-BP1 proteins. Niedzwiecka, A., Marcotrigiano, J., Stepinski, J., Jankowska-Anyszka, M., Wyslouch-Cieszynska, A., Dadlez, M., Gingras, A.C., Mak, P., Darzynkiewicz, E., Sonenberg, N., Burley, S.K., Stolarski, R. J. Mol. Biol. (2002) [Pubmed]
  12. Endotoxin (LPS) stimulates 4E-BP1/PHAS-I phosphorylation in macrophages. Potter, M.W., Shah, S.A., Elbirt, K.K., Callery, M.P. J. Surg. Res. (2001) [Pubmed]
  13. Complex formation between potyvirus VPg and translation eukaryotic initiation factor 4E correlates with virus infectivity. Léonard, S., Plante, D., Wittmann, S., Daigneault, N., Fortin, M.G., Laliberté, J.F. J. Virol. (2000) [Pubmed]
  14. Identification in the ancient protist Giardia lamblia of two eukaryotic translation initiation factor 4E homologues with distinctive functions. Li, L., Wang, C.C. Eukaryotic Cell (2005) [Pubmed]
  15. Critical residues for GTP methylation and formation of the covalent m7GMP-enzyme intermediate in the capping enzyme domain of bamboo mosaic virus. Huang, Y.L., Han, Y.T., Chang, Y.T., Hsu, Y.H., Meng, M. J. Virol. (2004) [Pubmed]
  16. The antiviral drug ribavirin does not mimic the 7-methylguanosine moiety of the mRNA cap structure in vitro. Westman, B., Beeren, L., Grudzien, E., Stepinski, J., Worch, R., Zuberek, J., Jemielity, J., Stolarski, R., Darzynkiewicz, E., Rhoads, R.E., Preiss, T. RNA (2005) [Pubmed]
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