Synthesis of the analogue nucleoside 3-deaza-2'-deoxycytidine and its template activity with DNA polymerase

Article abstract of DOI:10.1016/S0040-4020(99)00703-6

A new synthesis of the nucleoside analogue 3-deaza-2'-deoxycytidine is described. The N³-nitrogen of dC is involved in the central hydrogen bond of a dG-dC base pair. The relative importance of hydrogen bonding as a controlling factor in the activity of DNA polymerase is examined by studying both duplex stability and template effects for this dc³C nucleoside. Duplexes containing dG-dc³C base pairs were strongly destabilized while templates containing the analogue nucleoside were found to incorporate only the complementary dG triphosphate, similar to observations with templates containing the native 2'-deoxycytidine.