5′-Phosphouridine as a source of terminal phosphate groups in oligonucleotides

Abstract

A universal key component is proposed for the preparation of oligonucleotides with 3′- and 5′-terminal phosphate groups — 2′,3′-dibenzoyluridin-5′-yl (4-chlorophenylphosphate) (pU(Bz)2), which is a potential source of the phosphate group. The condensation ofpU(Bz)2 with the 5′-OH or the 3′-OH group of a protected oligonucleotide leads to the formation of oligodeoxyribonucleotides with 5′- or 3′-terminal uridine, respectively. The oxidation of the 2′,3′-cis-glycol group of the terminal uridine unit followed by β-elimination forms oligodeoxyribonucleotides with terminal phosphate groups.