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Nucleic Acids Research, 1994, Vol. 22, No. 8 1429-1436
© 1994

CHEMISTRY

Synthesis of oligodeoxynucleotides containing 2-thiopyrimidine residues - a new protection scheme

Robert G. Kuimelis and Krishnan P Nambiar*

Department of Chemistry, University of California Davis, CA 95616, USA

*To whom correspondence should be addressed

Received December 23, 1993. Revised March 7, 1994. Accepted March 7, 1994.

A method is described for the incorporation of 2'-de-oxy2-thlourldlne (dS2U) and 2'-deoxy-2-thlothymldlne (dS2T) into oligodeoxynucleotides at predetermined positions. This requires N3 orO4-acylation of dS2U and d32T with toluoyl chloride. These base-protected thlo-pyrlmldlnes are completely stable toward the aqueous iodine oxidation reagent used in the phosphoramldlte DNA synthesis method. The toluoyl protecting group is removed during the standard post-synthetic ammonia treatment. This novel protection strategy allows dS2U and d82T to be efficiently incorporated into oligodeoxynucleotides at predetermined sites without the usual problem of desutfurization and decomposition. Several 14-mers containing the Eco-RI recognition site (dGGCGGAAXXCCGCC and dGGCGGAAXXCGCGG, where X represents dT, dS2U or dS2T) have been synthesized and characterized by base composition, thermal denaturatlon, CD spectroscopy and endonuclease substrate activity.


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