Synthesis of an imidazole C-nucleoside phosphoramidite with POM as a protecting group

Abstract

To investigate the direct role of imidazole in RNA catalysis, we designed and synthesized an imidazole C-ribonucleoside phosphoramidite from tribenzylribofuranosylimidazole¹⁾ . This phosphoramidite can be readily used in conventional DNA/RNA synthesizer to incorporate imidazole into normal base position of RNA sequence. In the synthetic study, we demonstrate that pivaloyloxymethyl (POM) group is suitable as N-protecting group of imidazole in the synthesis of oligonucleosides. Use of POM group as a protecting group of imidazole was first reported in RNA synthesis.