Synthesis and properties of oligodeoxyribonucleotides containing the new base pairs, Im-N(O):Na-O(N) and Im-O(N):Na-N(O), with the ability to form four hydrogen bonds.

Abstract

Previously, we synthesized oligodeoxyribonucleotides (ODNs) containing novel base pairing motif consisting of tricyclic nucleosides, Im-N(O) and Im-O(N), with the ability to form four hydrogen bonds (H-bonds). When the base pair, Im-N(O):Im-O(N) pair, was incorporated into the duplex, thermal stability of the duplex depended on the sequence context. In this time, on the basis of previous results, we designed two new bicyclic nucleosides, Na-N(O) and Na-O(N) as complementary nucleobase of the tricyclic nucleobases. These nucleosides were synthesized via a Pd-mediated cross coupling reaction as a key step. When the new Im-O(N):Na-N(O) pair was incorporated into the duplex, it was remarkably stabilized independent of the sequence context.