DOI QR코드

DOI QR Code

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

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.

Keywords

References

  1. CRC Crit. Rev. Biochem. v.13 P. Modrich
  2. Biochemistry v.23 B. Connolly;B. Potter;F. Eckstein;A. Pingoud;L. Grotjahn
  3. J. Biol. Chem. v.259 B. Connolly;F. Eckstein;A. Pingoud
  4. J. Org. Chem. v.23 H. Tolkmith
  5. J. Org. Chem. v.23 H. Tolkmith
  6. J. Chem. Soc., Chem. Commun. O. Kemal;C. Reese;H. Serafinowska
  7. J. Biol. Chem. v.257 P. Romaniuk;F. Eckstein
  8. J. Biol. Chem. v.257 P. Bartlett;F. Eckstein
  9. J. Am. Chem. Soc. v.104 B. Gaffrey;R. Jones;G. S. Ti
  10. J. Chem. Soc., Chem. Commun. J. Chattopadhyaya;C. Reese
  11. Biochemistry v.24 R. Cosstick;F. Eckstein
  12. Tet. Lett. C. Reese;R. Titmus;L. Yau