Polynucleotides. III. Synthesis of Four Trinucleoside Diphosphates containing Tubercidin (7-Deazaadenosine) and N^6-Dimethyladenosine

概要

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Tubercidin (7-deazaadenosine) was converted to the 5'-O-monomethoxytrityl derivative, which was phosphorylated with P^1-diphenyl-P^2-morpholinopyrophosphorochloridate to afford the 2'-and 3'-monophosphates. The latter compound was acetylated to N, 2', 5'-tri-O-acetyltubercidin 3'-phosphate. N^6-Dimethyladenosine was converted to the 5'-benzoyl derivative which was phosphorylated with cyanoethyl phosphate and DCC to give the 2'-and 3'-monophosphates. N^6-Dimethyladenosine 3'-phosphate was protected by acetylation in the 2'-and 5'-positions. These protected 3'-phosphates were subjected to condensation with N, 2'-dibenzoyladenylyl-(3'→5')-N, 2', 3'-tribenzoyl-adenosine or N, 2'-dibenzoylcytidylyl-(3'→5')→N, 2', 3'-tribenzoylcytidine by the DCC procedure. The trinucleoside diphosphates 7-deazaadenylyl-(3'→5')-adenylyl-(3'→5')-adenosine, 7-deazaadenylyl-(3'→5')-cytidylyl-(3'→5')-cytidine, N^6-dimethyl-adenylyl-(3'→5')-adenylyl-(3'→5')-adenosine and N^6-dimethyladenylyl-(3'→5')-cytidylyl-(3'→5')-cytidine were purified by paper chromatography and paper electrophoresis. Complete digestion of these trinucleoside diphosphates with spleen phosphodiesterase established the 3'→5' phosphodiester linkages.
公益社団法人日本薬学会の論文
1966-12-25