Gluco- and ribosylation of the bases of sugar protected inosine and uridine were investigated, obtaining only adducts with beta -configuration at thenew 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 pyrophosphatebond formation.
Glycosylations of inosine and uridine nucleoside bases and synthesis of the new 1-(BETA-D-glucopyranosyl)-inosine-5’,6’’-diphosphate / A., De Capua; DE NAPOLI, Lorenzo; DI FABIO, Giovanni; A., Messere; Montesarchio, Daniela; Piccialli, Gennaro. - In: NUCLEOSIDES & NUCLEOTIDES. - ISSN 0732-8311. - ELETTRONICO. - 19:8(2000), pp. 1289-1299. [10.1080/15257770008033052]
Glycosylations of inosine and uridine nucleoside bases and synthesis of the new 1-(BETA-D-glucopyranosyl)-inosine-5’,6’’-diphosphate
DE NAPOLI, LORENZO;DI FABIO, GIOVANNI;MONTESARCHIO, DANIELA;PICCIALLI, GENNARO
2000
Abstract
Gluco- and ribosylation of the bases of sugar protected inosine and uridine were investigated, obtaining only adducts with beta -configuration at thenew 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 pyrophosphatebond formation.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
