SYNTHESIS AND CONFIGURATION ANALYSIS OF DIASTEREOMERS OF 5'-O-(2'-DEOXYCYTIDYL)-3'-O-THYMIDYL PHOSPHOROTHIOATE

Citation
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
Citations number
14
Categorie Soggetti
Chemistry
ISSN journal
02532964
Volume
17
Issue
1
Year of publication
1996
Pages
24 - 28
Database
ISI
SICI code
0253-2964(1996)17:1<24:SACAOD>2.0.ZU;2-C
Abstract
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.