Synthesis and properties of conformationally rigid cyclouridylic acid having a covalent bonding linker between the uracil 5-position and the 5 phosphate group

Article abstract of DOI:10.1016/0040-4039(95)02062-4

A novel cyclouridylic acid 1 having a propylene bridge between the uracil 5 position and the 5′-phosphate group was synthesized. The structure of 1 was analyzed by ¹H NMR, and CD spectroscopy, which suggested that the cyclonucleotide 1 was highly stabilized in a considerably rigid g′/C3′-endo conformation with the base orientation of and. The molecular mechanics calculation of 1 gave a similar conclusion.