A cytosine analogue containing a conformationally flexible acyclic linker for triplex formation at sites with contiguous G-C base pairs

Article abstract of DOI:10.1016/S0040-4020(97)10289-7

Two nucleoside derivatives of the pyrimidine bases T and m(5ox)C have been prepared with flexible acyclic carbohydrate linkers. A new procedure, beginning with (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol permits the preparation of the stereochemically pure acyclic derivatives of both protected nucleoside analogues without contamination by a problematic rearrangement product. By simply increasing the flexibility of the carbohydrate portion of the am(5ox)C nucleoside derivative. 15-mer triplexes containing five contiguous G-C base pairs exhibit a 7-8 °C increase in T(m) value.