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

Abstract

The synthesis of C4-linked imidazole C₀- and C₂-2′-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.

Key words

imidazole - phosphoramidite - C-deoxyribonucleoside - base pairing - DNA

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