title: 7,5'-O-dibenzylinosines: synthesis and studies on their conformational properties.
abstract: Reaction of 2',3'-O-isopropylidene inosine with benzyl bromide (1 h, rt) led to the 1,5'-O-dibenzylderivative 4, but by increasing the reaction time or the temperature, compound 4 is further transformed into the 1,7,5'-O-tribenzylinosine derivative 5. Similarly, the 7-methyl-1,5'-O-dibenzylderivative 6 has been synthesized from 4. The 1H-NMR spectra of 5 and 6 showed peculiar chemical shifts for geminal protons (H5' and H5'' of the ribose, and the CH2 of the benzyl groups). Preliminary NMR studies have been performed, including NOESY experiments that point toward the predominant existence of conformers that are stabilized by an electrostatic interaction between the positively charged imidazole of the base moiety and the high electron density of the 5'-benzyl substituent.
authors: Instituto de Química Médica (CSIC), Madrid, Spain.
authors: Elena
authors: E
authors: Casanova
authors: Leire
authors: L
authors: Aguado
authors: María-Luisa
authors: ML
authors: Jimeno
authors: Federico
authors: F
authors: Gago
authors: María-José
authors: MJ
authors: Camarasa
authors: María-Jesús
authors: MJ
authors: Pérez-Pérez
mesh_terms: D007288:Inosine / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D007288:Inosine