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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 17, Number 1
BKCSDE 17(1)
January 20, 1996

Title	Synthesis and Configuration Analysis of Diastereomers of 5'-O-(2'-Deoxycytidyl)-3'-O-Thymidyl Phosphorothioate
Author	Byung Jo Moon*, Hyun Ju Jeong, Sang Kook Kim, Nam Hee Kim
Keywords
Abstract	A procedure is described for the synthesis of the title compound via phosphotriester intermediates. The preparation of Rp and Sp 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 Rp and Sp follows from anaylsis of 31P NMR spectroscopy and reverse-phase HPLC and the stereospecificity in the hydrolysis catalyzed by Nuclease S1 and snake venom phosphodiesterase. Diastereomerically pure Rp and Sp d[Cp(S)T] were utilized to synthesize oligonucleotides containing the XhoI recognition sequence with a phosphorothioate group at the cleavage site.
Page	24 - 28
Full Text	PDF

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