Practical and Reliable Synthesis of 1,2-Dideoxy-d-ribofuranose and its Application in RNAi Studies

Abstract

ABSTRACT We developed a practical and reliable method for synthesizing an abasic deoxyribonucleoside, 1,2-dideoxy-d-ribofuranose (dRH) via elimination of nucleobase from thymidine. To synthesize oligonucleotides bearing dRH by the standard phosphoramidite solid-phase method, dRH was converted to the corresponding phosphoramidite derivative and linked to a solid support (controlled pore glass resin). Chemically modified small interfering RNAs (siRNAs) possessing dRH at their 3′-overhang regions were synthesized. Introducing dRH to the 3′-end of the antisense strand of siRNA reduced its knockdown effect.