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Nucleic Acids Research, 1990, Vol. 18, No. 4 829-835
© 1990

CHEMISTRY

Synthesis and properties of dithymidine phosphate analogues containing 3'-thiothymidine

Richard Cosstick* and Joseph S. Vyle

The Robert Robinson Laboratories, Department of Chemistry, University of Liverpool Liverpool L69 3BX, UK

*To whom correspondence should be addressed

Received November 13, 1989. Accepted December 11, 1989.

Dithymidine-3'-S-phosphorothioate (d(TspT)) has been prepared from a 5'-O-monomethoxytritylthymidine-3'-S- phosphorothioamidite (7) by activation with 5-(p- nitrophenyl)tetrazole in the presence of 3'-O- acetylthymidine. The resulting dinucleoside phosphorothioite is readily oxidised to the corresponding 3'-S-phosphorothioate using either tetrabutylammonium (TBA) perlodate or TBA oxone and has been deprotected under standard conditions to yield d(TspT). This dithymidine phosphate analogue is comparatively resistant to hydrolysis by nuclease P1, but the P-S bond is readily cleaved by aqueous solutions of either iodine or silver nitrate. Dithymidine-3'-S-phosphorodithioate (d[Tsp(s)T] was prepared in an analogous fashion using sulphur to oxidise the intermediate dinucleoside phosphoro thiolte. Absolute stereochemistry has been assigned to the diastereoisomers of d by comparing their physical and chemical properties to those of the dinucleoside phosphorothioates.


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