Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: Synthesis of thymidine dinucleotide analogs with triazole-modified backbones

Article abstract of DOI:10.1016/S0960-894X(97)00269-2

Novel backbone-modified dinucleotide analogs of types V and VI have been synthesized, where the natural phosphodiester linkage of a T-T dinucleotide has been replaced by a triazole heterocycle. The key step of the synthesis is the regioselective, thermal cycloaddition of a 2-oxoalkylidene triphenylphosphorane with an azide derivative to generate the triazole ring.