Biopolymers and cell. 2007; 23 (6): 538 - 543

Synthesis of (2'-5')-triadenylate and their analogues using O-nucleophilic catalysis of internucleotide coupling reaction

I. Ya. Dubey, L. V. Dubey

(2'-5')-triadenylate and its analogues containing 3'-terminal epoxyadenosine or cordycepin residue were obtained by phosphotriester approach in the presence of 4-ethoxypyridine N-oxide (EPO) as O-nucleophilic catalyst of coupling reaction. The coupling reactions proceeded with high speed (below 5 min) and efficiency (yield 86–92 %). The reaction yields achieved in the presence of N-methylimidazole were substantially lower (80–85 %), and the final yields of triadenylates were only 21–25 %, as compared to 29–35 % obtained with N-oxide.

Keywords: (2'-5')-oligoadenylates, oligonucleotide analogues, phosphotriester synthesis, nucleophilic catalysis, pyridine N-oxides.