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New oligodeoxyribonucleotide derivatives bearing internucleotide N-tosyl phosphoramidate groups: Synthesis and complementary binding to DNA and RNA


N-Sulfonyl phosphoramidate derivatives of oligodeoxyribonucleotides containing N-tosyl phosphoramidate groups are first reported. The synthesis is based on Staudinger reaction between tosyl azide and 3′,5′-dinucleoside β-cyanoethyl phosphite comprising the immobilized oligonucleotide, which is obtained by the phosphoramidite coupling during the solid-phase oligonucleotide synthesis. The N-tosyl phosphoramidate group was stable under conditions of the oligonucleotide synthesis, in particular, upon acidic detritylation followed by the removal of protective groups and cleavage from the polymer support by the treatment with concentrated aqueous ammonia at 55°C. The stability of DNA and RNA duplexes of the model oligonucleotides containing N-tosyl phosphoramidate groups was only slightly lower than that of native DNA:DNA and DNA:RNA duplexes, respectively.

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electrospray ionization


triethylammonium acetate


  1. Sharma, V.K., Sharma, R.K., and Singh, S.K., Med. Chem. Commun., 2014, vol. 5, pp. 1454–1471.

    CAS  Article  Google Scholar 

  2. McClorey, G. and Wood, M.J., Curr. Opin. Pharmacol., 2015, vol. 24, pp. 52–58.

    CAS  Article  PubMed  Google Scholar 

  3. Stephenson, M.L. and Zamecnik, P.C., Proc. Natl. Acad. Sci. U. S. A., 1978, vol. 75, pp. 285–288.

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  4. Eckstein, F., Antisense Nucleic Acid Drug Dev., 2009, vol. 10, pp. 117–121.

    Article  Google Scholar 

  5. Staudinger, H. and Meyer, J., Helv. Chim. Acta, 1919, vol. 2, pp. 635–646.

    CAS  Article  Google Scholar 

  6. Letsinger, R.L. and Schott, M.E., J. Am. Chem. Soc., 1981, vol. 103, pp. 7394–7396.

    CAS  Article  Google Scholar 

  7. Nielsen, J. and Caruthers, M.H., J. Am. Chem. Soc., 1988, vol. 110, pp. 6275–6276.

    CAS  Article  PubMed  Google Scholar 

  8. Heindl, D., Kessler, D., Schube, A., Thuer, W., and Giraut, A., Nucleic Acids Symp. Ser., 2008, vol. 52, pp. 405–406.

    CAS  Article  Google Scholar 

  9. Heindl, D. and Kessler, D., CA Patent No. 2627208, 2006.

    Google Scholar 

  10. Kupryushkin, M.S., Apukhtina, V.S., Vasil’eva, S.V., Pyshnyi, D.V., and Stetsenko, D.A., Izv. Akad. Nauk, Ser. Khim., 2015, no. 7, pp. 1678–1681.

    Google Scholar 

  11. Heydt, H., Regitz, M., Mapp, A.K., and Chen, B., p-Toluenesulfonyl azide, in Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons, Ltd., 2001.

    Google Scholar 

  12. Tian, W.Q. and Wang, Y.A., Org. Chem., 2004, vol. 69, pp. 4299–4308.

    CAS  Article  Google Scholar 

  13. Stetsenko, D.A., Kupryushkin, M.S., and Pyshnyi, D.V., Pat. Appl. no. WO2016/028187 A1, 2014.

    Google Scholar 

  14. Kupryushkin, M.S., Pyshnyi, D.V, and Stetsenko, D.A., Acta Naturae, 2014, vol. 6, pp. 123–125.

    Google Scholar 

  15. Xing, Y., Sheng, G., Wang, J., Lu, P., and Wang, Y., Org. Lett., 2014, vol. 16, pp. 1244–247.

    CAS  Article  PubMed  Google Scholar 

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Correspondence to D. A. Stetsenko.

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Original Russian Text © D.V. Prokhorova, B.P. Chelobanov, E.A. Burakova, A.A. Fokina, D.A. Stetsenko, 2017, published in Bioorganicheskaya Khimiya, 2017, Vol. 43, No. 1, pp. 45–50.

The paper is based on the materials of the “Chemical Biology 2016” conference; Novosibirsk, Russia, July 24–29, 2016.

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Prokhorova, D.V., Chelobanov, B.P., Burakova, E.A. et al. New oligodeoxyribonucleotide derivatives bearing internucleotide N-tosyl phosphoramidate groups: Synthesis and complementary binding to DNA and RNA. Russ J Bioorg Chem 43, 38–42 (2017).

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  • β-cyanoethyl phosphite
  • solid-phase synthesis
  • Staudinger reaction
  • p-toluenesulfonyl azide