Novel dinucleoside 5',5'-triphosphate cap analogues. Synthesis and affinity for murine translation factor eIF4E.
Chemical synthesis of a series of novel dinucleoside cap analogues, m7GpppN, where N is formycin A, 3'-O-methylguanosine, 9-beta-D-arabinofuranosyladenine, and isoguanosine, has been performed using our new methodology. The key reactions of pyrophosphate bonds formation were achieved in anhydrous dimethylformamide solutions employing the catalytic properties of zinc salts. Structures of the new cap analogues were confirmed by 1H NMR and 31p NMR spectra. The binding affinity of the new cap analogues for murine eIF4E(28-217) were determined spectroscopically showing the highest association constant for the analogue that contains formycin A.
Stepinski
Janusz
J
Department of Biophysics, Institute of Experimental Physics, Warsaw University, ul. Zwirki i Wigury 93, Warsaw 02-089, Poland. jastep@biogeo.uw.edu.pl
Zuberek
Joanna
J
Jemielity
Jacek
J
Kalek
Marcin
M
Stolarski
Ryszard
R
Darzynkiewicz
Edward
E
D000241:Adenosine; D000818:Animals; D004305:Dose-Response Relationship, Drug; D039561:Eukaryotic Initiation Factor-4E / Q000737:chemistry* / Q000235:genetics*; D005573:Formycins / Q000737:chemistry; D006151:Guanosine / Q000737:chemistry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008956:Models, Chemical; D009705:Nucleosides / Q000737:chemistry*; D009711:Nucleotides / Q000737:chemistry; D011485:Protein Binding; D012314:RNA Cap Analogs; D013053:Spectrophotometry; D013816:Thermodynamics; D014740:Vidarabine / Q000737:chemistry
D039561:Eukaryotic Initiation Factor-4E; D005573:Formycins; D009705:Nucleosides; D009711:Nucleotides; D012314:RNA Cap Analogs; D006151:Guanosine; C008184:isoguanosine; C034550:formycin; D014740:Vidarabine; D000241:Adenosine