title: Novel dinucleoside 5',5'-triphosphate cap analogues. Synthesis and affinity for murine translation factor eIF4E.
abstract: 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.
authors.affiliation: Department of Biophysics, Institute of Experimental Physics, Warsaw University, ul. Zwirki i Wigury 93, Warsaw 02-089, Poland. jastep@biogeo.uw.edu.pl
authors.forename: Janusz
authors.initials: J
authors.lastname: Stepinski
authors.forename: Joanna
authors.initials: J
authors.lastname: Zuberek
authors.forename: Jacek
authors.initials: J
authors.lastname: Jemielity
authors.forename: Marcin
authors.initials: M
authors.lastname: Kalek
authors.forename: Ryszard
authors.initials: R
authors.lastname: Stolarski
authors.forename: Edward
authors.initials: E
authors.lastname: Darzynkiewicz
mesh_terms: 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
chemical_list: 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