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Nucleic Acids Research, 1975, Vol. 2, No. 1 1-10
© 1975

Articles

The use of S-2-cyanoethyl phosphorothioate In the preparation of ollgo 5'-deoxy-5'-thlothymldylates

J. Kresse, K.L. Nagpal, J. Nagyvary* and J.T. Uchlc+

*Department of Biochemistry and Biophysics, Texas A&M University College Station, Texas 77843, USA

Received October 18, 1974.

An improvement of our strategy for the stepwise synthesis of oligo 5'-deoxy-5'-thiodeoxyribonucleotides [Chladek and Nagyvary (1972) J. Amer. Chem. Soc. 94, 2079] involves the use of 5'-0-tosylthymidine 3'-S-2-cyanoethyl phosohorothioate. The displacement of the tosylate by thymidine 3'-phosphorothioate and subsequent alkaline deblocking afforded the dinucleotide (Tps)2. The process of displacement and deblocking was repeated three more times at an average yield of 30 percent per step. The corresponding bifunctional derivative of deoxyadenosine was found much less reactive and practically unsuitable for repeated chain elongation. The ORD and CD spectra of the analogs are similar to those of the natural oligonucleotides.

+College of Pharmacy, University of Utah, Sait Lake City, Utach 84112, USA


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