Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Configuration Analysis of Diastereomers of 5'-O-(2'-Deoxycytidyl)-3'-O-Thymidyl Phosphorothioate

  • Published : 19960100
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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[Cp(S)T] was performed by the condensation of the protected deoxycytidine, the protected thymidine, 2,5-dichlorophenylphosphorodichloridothioate and 1-hydroxybenzotriazole in THF. Their designation of configuration at phosphorus as $R_p$ and $S_p$ follows from anaylsis of ${31}^P$ NMR spectroscopy and reverse-phase HPLC and the stereospecificity in the hydrolysis catalyzed by Nuclease S1 and snake venom phosphodiesterase. Diastereomerically pure $R_p$ and $S_p$ d[Cp(S)T] were utilized to synthesize oligonucleotides containing the XhoI recognition sequence with a phosphorothioate group at the cleavage site.

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References

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Cited by

  1. ChemInform Abstract: Synthesis and Configuration Analysis of Diastereomers of 5′-O-(2′- Deoxycytidyl)-3′-O-thymidyl Phosphorothioate. vol.27, pp.30, 1996, https://doi.org/10.1002/chin.199630285