Synthesis of Monomers Bearing at the 2′‐Position Cyanomethoxycarbonyl Group for Phosphoramidite Oligonucleotide Synthesis

Abstract

A novel series of phosphoroamidites for the synthesis of 2′‐modified oligonucleotides was designed and synthesized on the base of 2′‐amino uridine and 2′‐amino arabinoadenosine. The amino groups in these compounds were acidified by bis‐cyanomethyl esters of different dicarbonic acids. Generated reactive linker groups containing cyanomethoxycarbonyl groups are stable under conditions of oligonucleotide synthesis but could be easily functionalised in post‐synthetic stage by treatment with compounds bearing primary amino groups.

Keywords:

• Modified nucleosides
• Cyanomethyl esters, 2′‐amino uridine, 2′‐amino arabinoadenosine, Cyanomethoxycarbonyl
• Reactive linker groups

Acknowledgments

This work is supported by RFBR (02‐04‐48664‐a), Grants BRHE Rec‐008, Wellcome Trust (CRIG 063630) and Russian Science Support Foundation.