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.
- 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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