Biopolym. Cell. 2007; 23(6):538-544.
Bioorganic Chemistry
Synthesis of (2'-5')-triadenylate and their analogues using O-nucleophilic catalysis of internucleotide coupling reaction
1Dubey I. Ya., 1Dubey L. V.
  1. Institute of Molecular Biology and Genetics, NAS of Ukraine
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680

Abstract

(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

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