Bj. Moon et al., SYNTHESIS AND CONFIGURATION ANALYSIS OF DIASTEREOMERS OF 5'-O-(2'-DEOXYCYTIDYL)-3'-O-THYMIDYL PHOSPHOROTHIOATE, Bulletin of the Korean Chemical Society, 17(1), 1996, pp. 24-28
A procedure is described for the synthesis of the title compound via p
hosphotriester intermediates. The preparation of R(p) and S-p diastere
omeric dinucleotide of d[Cp(S)T] was performed by the condensation of
the protected deoxycytidine, the protected thymidine, 2,5-dichlorophen
ylphosphorodichloridothioate and 1-hydroxybenzotriazole in THF. Their
designation of configuration at phosphorus as R(p) and S-p follows fro
m anaylsis of P-31 NMR spectroscopy and reverse-phase HPLC and the ste
reospecificity in the hydrolysis catalyzed by Nuclease S1 and snake ve
nom phosphodiesterase. Diastereomerically pure R(p) and S-p d[Cp(S)T]
were utilized to synthesize oligonucleotides containing the XhoI recog
nition sequence with a phosphorothioate group at the cleavage site.