Deacylation of 2-N-isobutyryl- and 2-N-isobutyryl-6-O-methyl-2′-deoxyguanosine in the condensed and gas phase. A kinetic investigation

Abstract

The kinetics of deacyclation of 2-N-isobutyryl-2 and 2-N-isobutyryl-6-O-methyl-2′-deoxyguanosine 4 show that the former can be deblocked by ammonolysis, whereas the latter requires strong alkaline conditions. This different behaviour is correlated with the availability of the enolizable lactam function of the guanine ring. Similar effects are in operation in the unimolecular gas-phase dissociations of the same species.