Studies on Transfer Ribonucleic Acid and Related Compounds. XI. A Comparative Study on Condensing Reagents in Syntheses of Ribooligonucleotides
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概要
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Three types of condensation reaction shown in Chart (Scheme 1-3) were carried out. Scheme (1) shows a condensation of the protected mononucleotide with the protected nucleoside to give UpU. Scheme (2) shows a condensation of the mononucleotides and Scheme (3) involves a reaction of the dinucleotide blocks obtained in reaction (1) and (2). Reagents used for the first reaction were : dicyclohexylcarbodiimide, DCC ; triphenylphosphine-2,2'-dipyridyldisulfide, Ph_3P-(PyS-)_2 ; diphenylphosphoryl azide, DPPA ; diethylphosphoryl cyanide, DEPC ; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline, iBiBDQ : 2,4,6-triisopropylbenzenesulfonyl chloride, TPS ; p-toluenesulfonic anhydride, Ts_2O. DCC, TPS and Ph_3P-(PyS-)_2 gave almost quantitative yield to form the dinucleoside monophosphate. For the second and the third reactions above three activating reagents were used. These experiments showed that DCC seemed to be suitable for the synthesis of the dinucleotide using aromatic phosphoramidates as protection of the terminal phosphate and TPS for block condensation involving the protected UpU and UpUp to yield the tetranucleotide, UpUpUpU.
- 1975-10-25
著者
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大塚 栄子
Faculty Of Pharmaceutical Sciences Hokkaido University
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池原 森男
Faculty Of Pharmaceutical Sciences Osaka University
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杉山 孝
Faculty Of Pharmaceutical Sciences Osaka University
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