title: Glycosylations of inosine and uridine nucleoside bases and synthesis of the new 1-(beta-D-glucopyranosyl)-inosine-5',6"-diphosphate.
abstract: Gluco- and ribosylation of the bases of sugar protected inosine and uridine were investigated, obtaining only adducts with beta-configuration at the new glycosidic carbon; stereospecific insertion of a sugar moiety at the 1-N of inosine was achieved either using a Mitsunobu approach (for ribosylation) or by direct coupling of 1-alpha-bromoglucose 13 with 2',3',5'-tri-O-acetylinosine for glucosylation. 1-(beta-D-glucosyl)-inosine, chosen as starting substrate for glucosylated analogs of cyclic IDP-ribose, was phosphorylated at the primary hydroxyls and tested in intramolecular pyrophosphate bond formation.
authors.affiliation: Dipartimento di Chimica Organica e Biologica, Università degli Studi di Napoli Federico II, Italy.
authors.forename: A
authors.initials: A
authors.lastname: De Capua
authors.forename: L
authors.initials: L
authors.lastname: De Napoli
authors.forename: G
authors.initials: G
authors.lastname: Di Fabio
authors.forename: A
authors.initials: A
authors.lastname: Messere
authors.forename: D
authors.initials: D
authors.lastname: Montesarchio
authors.forename: G
authors.initials: G
authors.lastname: Piccialli
mesh_terms: D002236:Carbohydrate Conformation; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007288:Inosine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009705:Nucleosides / Q000737:chemistry*
chemical_list: C421447:1-glucopyranosylinosine-5',6'-diphosphate; D005960:Glucosides; D009705:Nucleosides; D007288:Inosine