Reaction of guanosine with glucose, ribose, and glucose 6-phosphate

The reaction of guanosine with glucose, glucose 6-phosphate or ribose in the presence of propylamine leads to the formation of several guanosine derivatives. During this process sugar degradation products are attached to the amino group of the guanosine residue. N2-(1-Carboxy-3,4-dihydroxybutyl)-guanosine, N2-(1-carboxyethyl)-guanosine, N2-[1-(N-propyl-carbamoyl)-ethyl]-guanosine, and N2-[1-(N-propyl-carbamoyl)-methyl]-guanosine have been isolated as pure compounds. N2-[1-(N-Propyl-carbamoyl)-3,4,5-trihydroxypentyl]-guanosine and N2-[1-(N-propyl-carbamoyl)-3,4-dihydroxybutyl]-guanosine, which were synthesized, can be detected in glucose- and ribose-guanosine reaction mixtures.