Synthesis of phosphorothioate analogues of oligoriboadenylates using salicylchlorophosphite

E. I. Kvasyuk, T. I. Kulak, I. A. Mikhailopulo

Institute of Bioorganic Chemistry, Academy of Sciences of the Byelorussian SSR, Minsk

Abstract: The phosphorothioate analogues of adenylyl(2'–5')adenosine, adenylyl(3'–5)-adenosine, adenylyl(5'–5')adenosine and adenylyl(2'–5')-P-thioadenylyl(3'–5')adenosine and adenylyl(2'–5')-P-thioadenylyl(2'–5')adenosine have been synthesized using salicylchlorophosphite for formation of internucleoside phosphodiester bonds. In the case of (2'–5') and (3'–5') dimers, all compounds were] obtained as individual Rp-and S_p-diastereosomers. The structure of the synthesized compounds was confirmed by UV, CD and ¹H NMR spectroscopy data, and enzymatic hydrolysis.

Russian Journal of Bioorganic Chemistry 1990, 16 (11):1537-1544

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