Structure determination of adducts from the reaction of (R)-glycidaldehyde and guanosine

The structures of the initial adducts formed in the reactions of guanosine or deoxyguanosine with (R)-glycidaldehyde have been determined and compared with those obtained from racemic glycidaldehyde. A new stable adduct has also been identified which is a potential biomarker for glycidaldehyde interactions with DNA. Mechanisms are proposed to account for the formation of all the observed products. The results provide information on the molecular basis for the genotoxicity of glycidaldehyde and compounds which generate this reactive aldehyde in vivo.