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We designed and synthesized four novel tricyclicnucleosides 1-4, which have imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine structures, to construct theramallystable, non-natural, DNA duplexes. Both 1:2 and 3:4 possess four complementary hydrogen-bond pairs and are expected to form more stable base-pairs than the naturally occurring Watson-Crick base-pairs when incorporated into oligodeoxynucleotides (ODNs). NMR studies of these base-pairs at the nucleoside level in CDCl3 identified the expected base-pair formation with four hydrogen bonds. We also synthesized several ODNs containing these nucleosides and measured their thermal stability. We found that if several of the novel base-pairs were incorporated on complementary strands, the resulting DNA duplexes had very high thermal stability.
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