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Synthesis of C4-Linked C0- and C2-Imidazole 2′-Deoxyribonucleoside Phos­phoramidites and Imidazole Base-Pairing Effects on DNA

The synthesis of C4-linked imidazole C 0 - and C 2 -2′-deoxyribonucleoside phosphoramidites (dPAs), in which the final phosphitylations are greatly improved by 4,5-dicyanoimidazole-promoted conversion, is described. The respective dPAs are successfully incorporated into the sequence of a 15-nt DNA, and the abilities of one or two imidazoles to pair with different bases are investigated through thermal melting ( T m ) experiments on the resulting DNA duplexes. Furthermore, computational models of the imidazole-modified DNAs are found to be in good agreement with the results of the thermal melting experiments.