Glycosylations of inosine and uridine nucleoside bases and synthesis of the new 1-(beta-D-glucopyranosyl)-inosine-5',6"-diphosphate.
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.
De Capua
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A
Dipartimento di Chimica Organica e Biologica, Università degli Studi di Napoli Federico II, Italy.
De Napoli
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L
Di Fabio
G
G
Messere
A
A
Montesarchio
D
D
Piccialli
G
G
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*
C421447:1-glucopyranosylinosine-5',6'-diphosphate; D005960:Glucosides; D009705:Nucleosides; D007288:Inosine