Deglycosylation of alkylated nucleosides: a molecular orbital study

Abstract

The glycoside bond in alkylated nucleosides is known to be more stable for $0^6$ -alkylguanosines and $0^4$ - alkylthymines, and less stable for $N^3$ - and $N^7$ -alkylpurine and $O^2$ - alkylpyrimidine nucleosides. These marked differences have been demonstrated through in vitro acidic hydrolysis and in vivo glycosylase repair. This study examines the relative facility of the deglycosylation reaction for various nucleosides through the use of theoretical indices derived from the semiempirical AM1 SCF-MO methodology, which furnish inferences much in consonance with experiment