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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 14, Number 1
BKCSDE 14(1)
January 20, 1993 

Synthesis and Configurational Analysis of Diastereomers of 5'-O-(2'-Deoxyadenosyl)-3'-O-(2'-deoxyadenosyl)-Phosphorothioate
Byung Jo Moon*, Kyung Lan Huh, Sang Kook Kim
A procedure is described for the synthesis of the title compound via phosphotriester intermediates. The preparation of Rp and Sp 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 Rp and Sp follows from analysis of 31P-NMR spectroscopy and reversed-phase HPLC and the stereospecificity in the hydrolysis catalyzed by nuclease Pl.
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