Synthesis and applications of oligoribonucleotides with selected 2′-O-methylation using the 2′-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl] protecting group

Abstract

The synthesis of base protected 5′-O-dimethoxytrityl-2′-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl]-3′-O-(2-cyanoethyl N,N-diisopropylphosphoramidites) is described, using phenoxyacetyl protection for the exocyclic amino groups of guanosine and adenosine and acetyl protection of the amino group of cytidine. High yield assembly of these building blocks into oligoribonucleotides on aminopropyl controlled pore glass was achieved using 5-(4-nitrophenyl)-1H-tetrazole as activator. Mixed sequences containing selected 2′-O-methylation were also synthesised and their significance for the study of RNA biochemistry is discussed.