Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Configurational Analysis of Diastereomers of $5^{\prime}-O-(2^{\prime}-Deoxyadenosyl)-3^{\prime}-O-(2^{\prime}$-deoxyadenosyl)-Phosphorothioate

  • Byung Jo Moon (Department of Biochemistry, College of Natural Sciences, Kyungpook National University) ;
  • Kyung Lan Huh (Department of Biochemistry, College of Natural Sciences, Kyungpook National University) ;
  • Sang Kook Kim (Department of Biochemistry, College of Natural Sciences, Kyungpook National University)
  • Published : 1993.02.20
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Abstract

A procedure is described for the synthesis of the title compound via phosphotriester intermediates. The preparation of $R_p\;and\;S_p$ diastereomeric dinucleotide of d[Ap(S)A] was performed by the condensation of protected deoxyadenosine, 2,5-dichlorophenylphosphorodichloridothioate and 1-hydroxybenzotriazole in THF. Their designation of configuration at phosphorus as $R_p\;and\;S_p$ follows from analysis of $^{31}P$-NMR spectroscopy and reversed-phase HPLC and the stereospecificity in the hydrolysis catalyzed by nuclease Pl.

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