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An azidomethyl protective group in the synthesis of oligoribonucleotides by the phosphotriester method

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Abstract

A rapid and effective method of an automatic oligoribonucleotide synthesis alternative to the phosphoramidite one was developed. This method is based on the phosphotriester approach to internucleotide bond formation under intramolecular O-nucleophilic catalysis and the use of an azidomethyl group for protection of a nucleotide 2′-hydroxyl function.

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Abbreviations

MTM:

methylthiomethyl group

NBS-C1:

2-nitrobenzenesulfenyl chloride

TBAF:

tetrabutylammonium fluoride

TIPDS-Cl2 :

1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane

TPS-C1:

2,4,6-triisopropylbenzenesulfonyl chloride

DBU:

1,8-diazabicyclo[5.4.0]undec-7-ene

References

  1. Sproat, B., Methods in Mol. Biol., 2005, vol. 288, pp. 17–31.

    CAS  Google Scholar 

  2. Efimov, V., Buryakova, A., Dubej, I., Polushin, N., Chakhmakhcheva, O., and Ovchinnikov, Yu., Nucleic Acids Res., 1986, vol. 14, pp. 6526–6540.

    Article  Google Scholar 

  3. Polushin, N., Smirnov, I., Verentchikov, A., and Coull, J., Tetrahedron Lett., 1996, vol. 37, pp. 3227–3230.

    Article  CAS  Google Scholar 

  4. Almer, H., Szabo, T., and Stawinski, J., Chem. Commun., 2004, pp. 290–291.

  5. Efimov, V.A., Molchanova, N.S., and Chakhmakhcheva, O.G., Nucleosides, Nucleotides and Nucleic Acids, 2007, vol. 26, pp. 1087–1093.

    Article  CAS  Google Scholar 

  6. Ogilvie, K.K., Sadana, K.L., Thompson, E.A., Quilliam, M.A., and Westmore, J.B., Tetrahedron Lett., 1974, vol. 15, pp. 2861–2863.

    Article  Google Scholar 

  7. Pitsch, S., Weiss, P.A., Jenny, L., Stutz, A., and Wu, X., Helv. Chem. Acta, 2001, vol. 84, pp. 3773–3795.

    Article  CAS  Google Scholar 

  8. Hartsel, S.A., Kitchen, D.E., Scaringe, S.A., and Marshall, W.S., Methods in Mol. Biol., 2005, vol. 288, pp. 33–50.

    CAS  Google Scholar 

  9. Zavgorodny, S.G., Pechenov, A.E., Shvets, V.I., and Miroshnikov, A.I., Nucleosides, Nucleotides and Nucleic Acids, 2000, vol. 19, pp. 1977–1991.

    Article  CAS  Google Scholar 

  10. Markiewicz, W.T., Biala, E., and Kierzek, R., Bull. Polish Academy of Sciences, Chemistry, 1984, vol. 32, pp. 433–451.

    CAS  Google Scholar 

  11. Zavgorodny, S., Polianski, M., Besidsky, E., Kriukov, V., Sanin, A., Pokrovskaya, M., Gurskaya, G., Lonnberg, H., and Azhayev, A., Tetrahedron Lett., 1991, vol. 32, pp. 7593–7596.

    Article  Google Scholar 

  12. Pechenov, A.E., Zavgorodny, S.G., Shvets, V.I., and Miroshnikov, A.I., Rus. J. Bioorg. Chem., 2000, vol. 26, pp. 327–333; Bioorg. Khim., 2000, vol. 26, pp. 362–368.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, GSP Moscow, 117997, Russia

    V. A. Efimov, A. V. Aralov, S. V. Fedunin, V. N. Klykov & O. G. Chakhmakhcheva

Authors
  1. V. A. Efimov
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  2. A. V. Aralov
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  3. S. V. Fedunin
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  4. V. N. Klykov
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  5. O. G. Chakhmakhcheva
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Corresponding author

Correspondence to V. A. Efimov.

Additional information

Original Russian Text © V.A. Efimov, A.V. Aralov, S.V. Fedunin, V.N. Klykov, O.G. Chakhmakhcheva, 2009, published in Bioorganicheskaya Khimiya, 2009, Vol. 35, No. 2, pp. 270–273.

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Efimov, V.A., Aralov, A.V., Fedunin, S.V. et al. An azidomethyl protective group in the synthesis of oligoribonucleotides by the phosphotriester method. Russ J Bioorg Chem 35, 250–253 (2009). https://doi.org/10.1134/S1068162009020149

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  • DOI: https://doi.org/10.1134/S1068162009020149

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