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

Abstract

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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Abbreviations

DMTr:

4,4′-dimethoxytrityl

ESI:

electrospray ionization

TEAA:

triethylammonium acetate

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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). https://doi.org/10.1134/S1068162017010071

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  • DOI: https://doi.org/10.1134/S1068162017010071

Keywords

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