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Furanopyrimidine (FPy) and 2,6-diamino-3-deazapurine (DC 3 Pu) nucleosides with the ability to interact in DDD and AAA H-bonding patterns, respectively, were prepared. The N-1 p Ka  value of the DC 3 Pu nucleoside was estimated to be 6.4, which is due to the lack of a nitrogen atom at the 3-position, suggesting that DC 3 Pu acts as a base interacting in a DDD H-bonding pattern under near physiological conditions. As DC 3 Pu and FPy are expected to form a thermally stable DDD:AAA type of base pair in an oligodeoxynucleotide (ODN) duplex, they were incorporated into ODNs, and the  Tm  value of the ODN duplex was determined. However, the ODN duplex containing a DC 3 Pu:FPy pair has a lower thermal stability than that containing a G:C pair does, although its thermal stability is equal to that of an ODN duplex with an A:T pair even under acidic conditions.

Synthesis and properties of oligonucleotides containing a 2,6-diamino-3-deazapurine:furanopyrimidine base pair