N,N′-Bis-(2-(cyano)ethoxycarbonyl)-2-methyl-2-thiopseudourea: A Guanylating Reagent for Synthesis of 2′-O-[2-(Guanidinium)ethyl]-Modified Oligonucleotides

Abstract

A guanylating reagent, N,N′-bis-(2-(cyano)ethoxycarbonyl)-2-thiopseudourea, was synthesized and used for synthesis of 2′-O-[2-(guanidinium)ethyl] (2′-O-GE) modified oligonucleotides. A convenient deprotection method for the 2′-O-GE oligonucleotides was developed.

Notes

^aConditions were Waters C-4 3.9 × 300 mm column; mobile phase A was 50 mM triethylammonium acetate; pH 7; mobile phase B was acetonitrile; gradient was 5% to 60% B in 55 minutes; flow rate 1.5 mL min⁻¹; detection at λ = 260.