Skip to main content
SpringerLink
Log in

Protective groups in the chemical synthesis of oligoribonucleotides

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

The methods of chemical oligoribonucleotide synthesis and the protective groups used are reviewed. The latest data on the protection of 2′-OH functions of nucleotide derivatives used as monomers for the RNA synthesis are comprehensively discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

EDA:

ethylenediamine

DBU:

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

DIPEA:

N,N-diisopropylethylamine

EEDQ:

ethyl 1,2-dihydro-2-ethoxy-1-quinoline carboxylate

MeIm:

1-methylimidazole

NBS-Cl:

2-nitrobenzenesulfenyl chloride

NMP:

1-methylpyrrolidin-2-one

Pac:

phenoxyacetyl

TBAF:

tetrabutylammonium fluoride

TfH:

trifluoromethane sulfonic acid

siRNA:

short interfering RNA

tRNAAla :

alanine transport RNA

tRNA Gly2 :

glycine transport RNA

References

  1. Yan, A.C., Bell, K.M., Breeden, M.M., and Ellington, A.D., Front. Biosci., 2005, vol. 10, pp. 1802–1827.

    Article  PubMed  CAS  Google Scholar 

  2. Bevilacqua, P.C. and Yajima, R., Curr. Opin. Chem. Biol., 2006, vol. 10, pp. 455–464.

    Article  PubMed  CAS  Google Scholar 

  3. Fire, A., Xu, S., Montgomery, M.K., Kostas, S.A., Driver, S.E., and Mello, C.C., Nature, 1998, vol. 391, pp. 806–811.

    Article  PubMed  CAS  Google Scholar 

  4. Elbashir, S.M., Harborth, J., Lendeckel, W., Yalcin, A., Weber, K., and Tuschl, T., Nature, 2001, vol. 411, pp. 494–498.

    Article  PubMed  CAS  Google Scholar 

  5. Dorsett, Y. and Tuschl, T., Nat. Rev. Drug Discovery, 2004, vol. 3, pp. 318–329.

    Article  CAS  Google Scholar 

  6. Bartel, D.P., Cell, 2004, vol. 116, pp. 281–297.

    Article  PubMed  CAS  Google Scholar 

  7. Reese, C.B., Tetrahedron, 1978, vol. 34, pp. 3143–3179.

    Article  CAS  Google Scholar 

  8. Oivanen, M., Kuusela, S., and Loennberg, H., Chem. Rev., 1998, vol. 98, pp. 961–990.

    Article  PubMed  CAS  Google Scholar 

  9. Acharya, S., Foldesi, A., and Chattopadhyaya, J., Org. Chem., 2003, vol. 68, pp. 1906–1910.

    Article  CAS  Google Scholar 

  10. Li, Y.F. and Breaker, R.R., J. Am. Chem. Soc., 1999, vol. 121, pp. 5364–5372.

    Article  CAS  Google Scholar 

  11. Reese, C.B., Org. Biomol. Chem., 2005, vol. 3, pp. 3851–3868.

    Article  PubMed  CAS  Google Scholar 

  12. Zon, G., Can. J. Chem., 2007, vol. 85, pp. 257–260.

    Article  CAS  Google Scholar 

  13. Somoza, A., Chem. Soc. Rev., 2008, vol. 37, pp. 2668–2675.

    Article  PubMed  CAS  Google Scholar 

  14. Beaucage, S.L. and Reese, C.B., in Current Protocols in Nucleic Acid Chemistry, Egli, M., Herdewijn, P., Matusda, A., and Sanghvi, Y.S, Eds., Wiley, 2009, pp. 2.16.1–2.16.31.

  15. Schaller, H., Weimann, G., Lerch, B., and Khorana, H.G., J. Am. Chem. Soc., 1963, vol. 85, pp. 3821–3827.

    Article  CAS  Google Scholar 

  16. Chattopadhyaya, J.B. and Reese, C.B., J. Chem. Soc., Chem. Commun., 1978, pp. 639–640.

  17. Sonveaux, E., in Protocols for Oligonucleotide Conjugates: Synthesis and Analytical Techniques, Agrawal, S., Eds., Totowa, N.J.: Humana Press, 1994, pp. 1–71.

    Chapter  Google Scholar 

  18. Pathak, T. and Chattopadhyaya, J., Acta Chem. Scand., 1985, vol. 39, pp. 799–806.

    Article  Google Scholar 

  19. van Boom, J.H. and Burgers, P.M.J., Tetrahedron Lett., 1976, pp. 4875–4878.

  20. Chattopadhyaya, J.B., Reese, C.B., and Todd, A.H., J. Chem. Soc., Chem. Commun., 1979, pp. 987–988.

  21. Brown, J.M., Christodoulou, C., Jones, S.S., Modak, A.S., Reese, C.B., Sibanda, S., and Ubasawa, A., J. Chem. Soc., Perkin Trans., 1989, vol. 1, pp. 1735–1750.

    Article  Google Scholar 

  22. Rao, M.V., Reese, C.B., Schehlmann, V., and Yu, P.S., J. Chem. Soc., Perkin Trans., 1993, vol. 1, pp. 43–55.

    Article  Google Scholar 

  23. Vinayak, R., Anderson, P., McCollum, C., and Hampel, A., Nucleic Acids Res., 1992, vol. 20, pp. 1265–1269.

    Article  PubMed  CAS  Google Scholar 

  24. McBride, L.J., Kierzek, R., Beaucage, S.L., and Caruther, M.H., J. Am. Chem. Soc., 1986, vol. 108, pp. 2040–2048.

    Article  CAS  Google Scholar 

  25. Ohkubo, A., Kuwayama, Y., Nishino, Y., Tsunoda, H., Seio, K., and Sekine, M., Org. Lett., 2010, vol. 12, pp. 2496–2499.

    Article  PubMed  CAS  Google Scholar 

  26. Jones, S.S., Reese, C.B., Sibanda, S., and Ubasawa, A., Tetrahedron Lett., 1981, vol. 22, pp. 4755–4758.

    Article  CAS  Google Scholar 

  27. Reese, C.B. and Skone, P.A., J. Chem. Soc., Perkin Trans., 1984, vol. 1, pp. 1263–1271.

    Article  Google Scholar 

  28. Reese, C.B. and Zard, L., Nucleic Acids Res., 1981, vol. 9, pp. 4611–4626.

    Article  PubMed  CAS  Google Scholar 

  29. Kamimura, T., Tsuchiya, M., Urakami, K., Koura, K., Sekine, M., Shinozaki, K., Miura, K., and Hata, T., J. Am. Chem. Soc., 1984, vol. 106, pp. 4552–4557.

    Article  CAS  Google Scholar 

  30. Sinha, N.O., Biernat, J., and Koster, H., Tetrahedron Lett., 1983, vol. 24, pp. 5843–5846.

    Article  CAS  Google Scholar 

  31. Reese, C.B., Colloq. Int. Cent. Natl. Rech. Sci., 1970, vol. 182, pp. 319–328.

    Google Scholar 

  32. Reese, C.B., Titmas, R.C., and Yau, L., Tetrahedron Lett., 1978, vol. 30, pp. 2727–2730.

    Article  Google Scholar 

  33. Honda, S., Urakami, K., Koura, K., Terada, K., Sato, Y., Kohno, K., Sekine, M., and Hata, T., Tetrahedron, 1984, vol. 40, pp. 153–163.

    Article  CAS  Google Scholar 

  34. Efimov, V.A., Aralov, A.V., Fedunin, C.D., Klykov, V.N., and Chakhmakhcheva, O.G., Russ. J. Bioorg. Chem., 2009, vol. 35, pp. 250–253.

    Article  CAS  Google Scholar 

  35. Efimov, V.A., Aralov, A.V., Klykov, V.N., and Chakhmakhcheva, O.G., Nucleosides Nucleotides Nucleic Acids, 2009, vol. 28, pp. 846–865.

    Article  PubMed  CAS  Google Scholar 

  36. Griffin, B.E., Reese, C.B., Stephenson, G.F., and Trentham, D.R., Tetrahedron Lett., 1966, pp. 4349–4354.

  37. Reitz, G. and Pfleiderer, W., Chem. Ber., 1975, vol. 108, pp. 2878–2894.

    Article  CAS  Google Scholar 

  38. Ohtsuka, E., Tanaka, S., and Ikehara, M., J. Am. Chem. Soc., 1978, vol. 100, pp. 8210–8213.

    Article  CAS  Google Scholar 

  39. Hayes, J.A., Brunden, M.J., Gilham, P.T., and Gough, G.R., Tetrahedron Lett., 1985, vol. 26, pp. 2407–2410.

    Article  CAS  Google Scholar 

  40. Ohtsuka, E. and Iwai, S., in Synthesis and Applications of DNA and RNA, Narang, S.A., Ed., San Diego: Academic Press, 1987, pp. 115–136.

    Chapter  Google Scholar 

  41. Takaku, H. and Kamaike, K., Chem. Lett., 1982, pp. 189–192.

  42. Takaku, H., Kamaike, K., and Tsuchiya, H., Org. Chem., 1984, vol. 49, pp. 51–56.

    Article  CAS  Google Scholar 

  43. Takaku, H., Ito, T., and Iwai, K., Chem. Lett., 1986, pp. 1005–1008.

  44. Klösel, R., König, S., Lahnhoff, S., and Karl, R.M., Tetrahedron Lett., 1996, vol. 52, pp. 1493–1502.

    Google Scholar 

  45. Saneyoshi, H., Ando, K., Seio, K., and Sekine, M., Tetrahedron, 2007, vol. 63, pp. 11195–11203.

    Article  CAS  Google Scholar 

  46. Tanaka, S., Hirakawa, T., Oishi, K., Hayakawa, Y., and Kitamura, M., Tetrahedron Lett., 2007, vol. 48, pp. 7320–7322.

    Article  CAS  Google Scholar 

  47. Stork, G. and Hudrlik, P.F., J. Am. Chem. Soc., 1968, vol. 90, pp. 4462–4464.

    Article  CAS  Google Scholar 

  48. Corey, E.J. and Venkateswarlu, A., J. Am. Chem. Soc., 1972, vol. 94, pp. 6190–6191.

    Article  CAS  Google Scholar 

  49. Ogilvie, K.K., Sadana, K.L., Thompson, A.E., Quillian, M.A., and Westmore, J.B., Tetrahedron Lett., 1974, pp. 2861–2863.

  50. Damha, M.J. and Ogilvie, K.K., in Protocols for Oligonucleotides and Analogs, Agrawal, S., Ed., Totowa, N.J.: Humana Press, 1993, pp. 81–114.

    Chapter  Google Scholar 

  51. Rozners, E., Westman, W., and Stromberg, R., Nucleic Acids Res., 1994, vol. 22 P, pp. 94–99.

    Article  Google Scholar 

  52. Sproat, B.S., Calonna, F., Mullah, B., Tsou, D., Andrus, A., Hampel, A., and Vinayak, R., Nucleosides Nucleotides, 1995, vol. 14, pp. 255–273.

    Article  CAS  Google Scholar 

  53. Brown, T. and Brown, D.J.S., in Oligonucleotides and Analogues. A Practical Approach, Eckstein, F., Ed., Oxford: IRL Press, 1991, pp. 1–24.

    Google Scholar 

  54. Stawinski, J., Stromberg, R., Thélin, M., and Westman, E., Nucleic Acids Res., 1988, vol. 16, pp. 9285–9298.

    Article  PubMed  CAS  Google Scholar 

  55. Chaix, C., Molko, D., and Teoule, R., Tetrahedron Lett., 1989, vol. 30, pp. 71–74.

    Article  CAS  Google Scholar 

  56. Mullah, B. and Andrus, A., Nucleosides Nucleotides, 1996, vol. 15, pp. 419–430.

    Article  CAS  Google Scholar 

  57. Goodwin, J.T., Stanick, W.A., and Glick, G.D., Org. Chem., 1994, vol. 59, pp. 7941–7943.

    Article  CAS  Google Scholar 

  58. Wincott, F., DiRenzo, A., Shaffer, C., Grimm, S., Tracz, D., Workman, C., Sweedler, D., Gonzalez, C., Scaringe, S., and Usman, N., Nucleic Acids Res., 1995, vol. 23, pp. 2677–2684.

    Article  PubMed  CAS  Google Scholar 

  59. Gasparutto, D., Livache, T., Bazin, H., Duplaa, A.-M., Guy, A., Khorlin, A., Molko, D., Roget, A., and Teoule, R., Nucleic Acids Res., 1992, vol. 20, pp. 5159–5166.

    Article  PubMed  CAS  Google Scholar 

  60. Westman, E. and Strömberg, R., Nucleic Acids Res., 1994, vol. 22, pp. 2430–2431.

    Article  PubMed  CAS  Google Scholar 

  61. Zewge, D., Gosselin, F., Sidler, R., DiMichele, L., and Cvetovich, R.J., Org. Chem., 2010, vol. 75, pp. 5305–5307.

    Article  CAS  Google Scholar 

  62. Pfister, M., Schirmeister, H. and Pfleiderer, W., Helv. Chim. Acta, 1994, vol. 77, pp. 10–22.

    Article  Google Scholar 

  63. Schirmeister, H., Mohr, M., Farkas, S., Stengele, K.-P., Reiner, T., Dunkel, M., Gokhale, S., Charubala, R., and Pfleiderer, W., Helv. Chim. Acta, 1995, vol. 7, pp. 1705–1737.

    Google Scholar 

  64. Capaldi, D.C. and Reese, C.B., Nucleic Acids Res., 1994, vol. 22, pp. 2209–2216.

    Article  PubMed  CAS  Google Scholar 

  65. Smith, M., Rammler, D.H., Goldberg, I.H., and Khorana, H.G., J. Am. Chem. Soc., 1962, vol. 84, pp. 430–440.

    Article  CAS  Google Scholar 

  66. Smrt, J. and Šorm, F., Collect. Czech. Chem. Commun., 1962, vol. 27, pp. 73–86.

    Google Scholar 

  67. Griffin, B.E. and Reese, C.B., Tetrahedron Lett., 1964, pp. 2925–2931.

  68. Reese, C.B., Saffhill, R., and Sulston, J.E., J. Am. Chem. Soc., 1967, vol. 89, pp. 3366–3368.

    Article  CAS  Google Scholar 

  69. Reese, C.B., Saffhill, R., and Sulston, J.E., Tetrahedron, 1970, vol. 26, pp. 1023–1030.

    Article  PubMed  CAS  Google Scholar 

  70. Norman, D.G., Reese, C.B., and Serafinowska, H.T., Tetrahedron Lett., 1984, vol. 25, pp. 3015–3018.

    Article  CAS  Google Scholar 

  71. Jones, S.S., Rayner, B., Reese, C.B., Ubasawa, A., and Ubasawa, M., Tetrahedron, 1980, vol. 36, pp. 3075–3085.

    Article  CAS  Google Scholar 

  72. Jones, S.S., Reese, C.B., and Sibanda, S., in Current Trends in Organic Synthesis, Nozaki, H., Ed., Oxford: Pergamon Press, 1983, pp. 71–81.

    Google Scholar 

  73. Brown, J.M., Christodoulou, C., Modak, A.S., Reese, C.B., and Serafinowska, H.T., J. Chem. Soc. Perkin Trans., 1989, vol. 1, pp. 1751–1767.

    Article  Google Scholar 

  74. Ohtsuka, E., Yamane, A., Doi, T., and Ikehara, M., Tetrahedron, 1984, vol. 40, pp. 47–57.

    Article  CAS  Google Scholar 

  75. Kruse, C.G., Jonkers, F.L., Dert, V., and van der Gen, A., Rec. Trav. Chim., 1979, vol. 98, pp. 371–380.

    Article  CAS  Google Scholar 

  76. Christodoulou, C., Agrawal, S., and Gait, M.J., Tetrahedron Lett., 1986, vol. 27, pp. 1521–1522.

    Article  CAS  Google Scholar 

  77. Reese, C.B. and Skone, P.A., Nucleic Acids Res., 1985, vol. 13, pp. 5215–5231.

    Article  PubMed  CAS  Google Scholar 

  78. Kierzek, R., Nucleosides Nucleotides, 1994, vol. 13, pp. 1757–1768.

    Article  CAS  Google Scholar 

  79. Iwai, S. and Ohtsuka, E., Nucleic Acids Res., 1988, vol. 16, pp. 9443–9456.

    Article  PubMed  CAS  Google Scholar 

  80. Lehmann, C., Xu, Y.-Z., Christodoulou, C., Tan, Z.-K., and Gait, M.J., Nucleic Acids Res., 1989, vol. 17, pp. 2379–2390.

    Article  PubMed  CAS  Google Scholar 

  81. Reese, C.B., Serafinowska, H.T., and Zappia, G., Tetrahedron Lett., 1986, vol. 27, pp. 2291–2294.

    Article  CAS  Google Scholar 

  82. Rao, T.S., Reese, C.B., Serafinowska, H.T., Takaku, H., and Zappia, G., Tetrahedron Lett., 1987, vol. 28, pp. 4897–4900.

    Article  CAS  Google Scholar 

  83. Sakatsume, O., Ohtsuki, M., Takaku, H., and Reese, C.B., Nucleic Acids Res., 1989, vol. 17, pp. 3689–3697.

    Article  PubMed  CAS  Google Scholar 

  84. Reese, C.B. and Thompson, E.A., J. Chem. Soc., Perkin Trans., 1988, vol. 1, pp. 2881–2885.

    Article  Google Scholar 

  85. Beijer, B., Sulston, I., Sproat, B.S., Rider, P., Lamond, A.I., and Neuner, P., Nucleic Acids Res., 1990, vol. 18, pp. 5143–5151.

    Article  PubMed  CAS  Google Scholar 

  86. Pieles, U., Beijer, B., Bohmann, K., and Weston, S., O’Loughlin S., Adam V., Sproat B.S, J. Chem. Soc., Perkin Trans., 1994, vol. 1, pp. 3423–3429.

    Article  Google Scholar 

  87. Sproat, B.S., Beijer, B., Groetli, M., Ryder, U., Morand, K.L., and Lamond, A.I., J. Chem. Soc., Perkin Trans., 1994, vol. 1, pp. 419–431.

    Article  Google Scholar 

  88. Rao, M.V. and Macfarlane, K., Nucleosides Nucleotides, 1995, vol. 14, pp. 911–915.

    Article  CAS  Google Scholar 

  89. McGregor, A., Rao, M.V., Duckworth, G., Stockley, P.G., and Connolly, B.A., Nucleic Acids Res., 1996, vol. 24, pp. 3173–3180.

    Article  PubMed  CAS  Google Scholar 

  90. Lloyd, W., Reese, C.B., Song, Q., Vandersteen, A.M., Visintin, C., and Zhang, P.-Z., J. Chem. Soc., Perkin Trans., 2000, vol. 1, pp. 165–176.

    Article  Google Scholar 

  91. Pon, R.T., Yu, S., Prabhavalkar, T., Mishra, T., Kulkarni, B., and Sanghvi, Y.S., Nucleosides Nucleotides Nucleic Acids, 2005, vol. 24, pp. 777–781.

    Article  PubMed  CAS  Google Scholar 

  92. Sandström, A., Kwiatkowski, M., and Chattopadhyaya, J., Acta Chem. Scand. B, 1985, vol. 39, pp. 273–290.

    Article  PubMed  Google Scholar 

  93. Rastogi, H. and Usher, D.A., Nucleic Acids Res., 1995, vol. 23, pp. 4872–4877.

    Article  PubMed  CAS  Google Scholar 

  94. Matysiak, M., Fitznar, H.-P., Schnell, R., and Pfleiderer, W., Helv. Chim. Acta, 1998, vol. 81, pp. 1545–1566.

    Article  CAS  Google Scholar 

  95. Matysiak, M. and Pfleiderer, W., Helv. Chim. Acta, 2001, vol. 84, pp. 1066–1085.

    Article  CAS  Google Scholar 

  96. Umemoto, T. and Wada, T., Tetrahedron Lett., 2004, vol. 45, pp. 9529–9531.

    Article  CAS  Google Scholar 

  97. Schwartz, M.E., Breaker, R.R., Asteriadis, G.T., Bear, J.S., and Gough, G.R., Bioorg. Med. Chem. Lett., 1992, vol. 2, pp. 1019–1024.

    Article  CAS  Google Scholar 

  98. Gough, G.R., Miller, T.J., and Mantick, N.A., Tetrahedron Lett., 1996, vol. 37, pp. 981–982.

    Article  CAS  Google Scholar 

  99. Cies-lak, J., Kauffman, J.S., Kolodziejski M.J., Lloyd, J.R., and Beaucage, S.L., Org. Lett., 2007, vol. 9, pp. 671–674.

    Article  CAS  Google Scholar 

  100. Cies-lak, J., Grajkowski, A., Kauffman, J.S., Duff, R.J., and Beaucage, S.L., Org. Chem., 2008, vol. 73, pp. 2774–2783.

    Article  CAS  Google Scholar 

  101. Wincott, F.E. and Usman, N., Tetrahedron Lett., 1994, vol. 35, pp. 6827–6830.

    Article  CAS  Google Scholar 

  102. Wada, T., Tobe, M., Nagayama, T., Furusawa, K., and Sekine, M., Tetrahedron Lett., 1995, vol. 36, pp. 1683–1684.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  104. Ohgi, T., Masutomi, Y., Ishiyama, K., Kitagawa, H., Shiba, Y., and Yano, J., Org. Lett., 2005, vol. 7, pp. 3477–3480.

    Article  PubMed  CAS  Google Scholar 

  105. Shiba, Y., Masuda, H., Watanabe, N., Ego, T., Takagaki, K., Ishiyama, K., Ohgi, T., and Yano, J., Nucleic Acids Res., 2007, vol. 35, pp. 3287–3296.

    Article  PubMed  CAS  Google Scholar 

  106. Zhou, C., Honcharenko, D., and Chattapadhyaya, J., J. Org. Biomol. Chem., 2007, vol. 5, pp. 333–343.

    Article  CAS  Google Scholar 

  107. Semenyuk, A., Földesi, A., Johansson, T., Estmer-Nilsson, C., Blomgren, P., Brannvall, M., Kirsebom, L., and Kwiatkowski, M., J. Am. Chem. Soc., 2006, vol. 128, pp. 12356–12357.

    Article  PubMed  CAS  Google Scholar 

  108. Tomaya, K., Takahashi, M., Minakawa, N., and Matsuda, A., Org. Lett., 2010, vol. 12, pp. 3836–3839.

    Article  PubMed  CAS  Google Scholar 

  109. Hata, T. and Azizian, J., Tetrahedron Lett., 1969, vol. 51, pp. 4443–4446.

    Article  CAS  Google Scholar 

  110. Scaringe, S.A., Wincott, F.E., and Caruthers, M.H., J. Am. Chem. Soc., 1998, vol. 120, pp. 11820–11821.

    Article  CAS  Google Scholar 

  111. Scaringe, S.A., Methods, 2001, vol. 23, pp. 206–217.

    Article  PubMed  CAS  Google Scholar 

  112. Hartsel, S.A., Kitchen, D.E., Scaringe, S.S., and Marshall, W.S., in Methods in Molecular Biology, Herdewijn, P., Ed., Totowa, N.J.: Humana Press, 2005, vol. 288, pp. 33–49.

    Google Scholar 

  113. Scaringe, S.A., Kitchen, D., Kaiser, R.J., and Marshall, W.S., in Current Protocols in Nucleic Acid Chemistry, Egli, M., Herdewijn, P., Matusda, A., and Sanghvi, Y.S, Eds., Wiley, 2004, pp. 2.10.1–2.10.16.

  114. Reese, C.B. and Trentham, D.R., Tetrahedron Lett., 1965, pp. 2467–2472.

  115. Fromageot, H.P.M., Reese, C.B., and Sulston, J.E., Tetrahedron, 1968, vol. 24, pp. 3533–3540.

    Article  CAS  Google Scholar 

  116. Kempe, T., Chow, F., Sundquist, W.I., Nardi, T.J., Paulson, B., and Peterson, S.M., Nucleic Acids Res., 1982, vol. 10, pp. 6695–6714.

    Article  PubMed  CAS  Google Scholar 

  117. Rozners, E., Renhofa, R., Petrova, M., Popelis, J., Kumpins, V., and Bizdena, E., Nucleosides Nucleotides, 1992, vol. 11, pp. 1579–1593.

    Article  CAS  Google Scholar 

  118. Lackey, J.G., Sabatino, D., and Damha, M.J., Org. Lett., 2007, vol. 9, pp. 789–792.

    Article  PubMed  CAS  Google Scholar 

  119. Lackey, J.G., Mitra, D., Somoza, M.M., Cerrina, F., and Damha, M.J., J. Am. Chem. Soc., 2009, vol. 131, pp. 8496–8502.

    Article  PubMed  CAS  Google Scholar 

  120. Johnsson, R., Lackey, J.G., Bogojeski, J.J., and Damha, M.J., Bioorg. Med. Chem. Lett., 2011, vol. 21, pp. 3721–3725.

    Article  PubMed  CAS  Google Scholar 

  121. Parey, N., Baraguey, C., Vasseur, J.-J., and Debart, F., Org. Lett., 2006, vol. 8, pp. 3869–3872.

    Article  PubMed  CAS  Google Scholar 

  122. Lavergne, T., Parey, N., Vasseur, J.-J., and Debart, F., Eur. J. Org. Chem., 2009, vol. P, pp. 2190–2194.

    Article  CAS  Google Scholar 

  123. Lavergne, T., Baraguey, C., Dupouy, C., Parey, N., Wuensche, W., Sczakiel, G., Vasseur, J.-J., and Debart, F., Org. Chem., 2011, vol. 76, pp. 5719–5731.

    Article  CAS  Google Scholar 

  124. Martin, A.R., Lavergne, T., Vasseur, J.-J., and Debart, F., Bioorg. Med. Chem. Lett., 2009, vol. 19, pp. 4046–4049.

    Article  PubMed  CAS  Google Scholar 

  125. Lavergne, T., Bertrand, J.-R., Vasseur, J.-J., and Debart, F., Chem.-Eur. J., 2008, vol. 14, pp. 9135–9138.

    Article  PubMed  CAS  Google Scholar 

  126. Lavergne, T., Martin, A., Debart, F., and Vasseur, J.-J., Nucleic Acids Symp. Ser. 2008, vol. 52, pp. 51–52.

    Article  CAS  Google Scholar 

  127. Lavergne, T., Janin, M., Dupouy, C., Vasseur, J.-J., and Debart, F., in Current Protocols in Nucleic Acid Chemistry, Egli, M., Herdewijn, P., Matusda, A., and Sanghvi, Y.S., Eds., Wiley, 2010, pp. 3.19.1–3.19.27.

  128. Dellinger, D.J., Timar, Z., Myerson, J., Sierzchala, A.B., Turner, J., Ferreira, F., Kupihar, Z., Dellinger, G., Hill, K.W., Powell, J.A., Sampson, J.R., and Caruthers, M.H., J. Am. Chem. Soc., 2011, vol. 133, pp. 11540–11556.

    Article  PubMed  CAS  Google Scholar 

  129. Wada, T., Mochizuki, A., Higashiya, S., Tsuruoka, H., Kawahar, S., Ishikawa, M., and Sekine, M., Tetrahedron Lett., 2001, vol. 42, pp. 9215–9219.

    Article  CAS  Google Scholar 

  130. Efimov, V.A., Aralov, A.V., Grachev, S.A., and Chakhmakhcheva, O.G., Russ. J. Bioorg. Chem., 2010, vol. 36, pp. 628–633.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

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

    A. V. Aralov & O. G. Chakhmakhcheva

Authors
  1. A. V. Aralov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. G. Chakhmakhcheva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Aralov.

Additional information

Original Russian Text © A.V. Aralov, O.G. Chakhmakhcheva, 2013, published in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 1, pp. 3-225.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Aralov, A.V., Chakhmakhcheva, O.G. Protective groups in the chemical synthesis of oligoribonucleotides. Russ J Bioorg Chem 39, 1–21 (2013). https://doi.org/10.1134/S1068162013010020

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162013010020

Keywords

Search

Navigation