Abstract
A new synthesis of the nucleoside analogue 3-deaza-2′-deoxycytidine is described. The N 3-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 dc 3C nucleoside. Duplexes containing dG-dc 3C 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.
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