Skip to main content
SpringerLink
Log in

Modification of nucleic acids using [3 + 2]-dipolar cycloaddition of azides and alkynes

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

Abstract

The use of azide and alkyne cycloaddition reaction in the synthesis of conjugates of nucleic acids and oligodeoxyribonucleotides is reviewed. Data on the chemical and enzymatic methods for introducing azides and alkynes into DNA are summarized.

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

NA:

nucleic acids

3′-AZT:

3′-azido-3′-deoxythymidine

CuAAC:

Cu(I)-catalyzed azide-alkyne cycloaddition

DBU:

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

DIEA:

diisopropylethylamine

Dmt:

4,4′-dimethoxytrityl

TBTA:

tris(1-benzyl-1,2,3-triazol-4-ylmethyl)amine

TCEP:

tris(2-carboxyethyl)phosphine

THPTA:

tris[1-(3-hydroxypropyl)-1,2,3-triazol-4-ylmethyl]amine

References

  1. Davy, E., Ann. Pharm., 1837, vol. 23, pp. 144–146.

    Article  Google Scholar 

  2. Grieß, P., Phil. Trans. R. Soc. Lond., 1864, vol. 154, pp. 733–755.

    Article  Google Scholar 

  3. Michael, A., J. Prakt. Chem., 1893, vol. 48, pp. 94–95.

    Article  Google Scholar 

  4. Huisgen, R., Angew. Chem., Int. Ed. Engl., 1963, vol. 2, pp. 565–598.

    Article  Google Scholar 

  5. Huisgen, R., Angew. Chem., Int. Ed. Engl., 1963, vol. 2, pp. 633–645.

    Article  Google Scholar 

  6. Tornøe, C.W., Christensen, C., and Meldal, M., J. Org. Chem., 2002, vol. 67, pp. 3057–3064.

    Article  PubMed  CAS  Google Scholar 

  7. Rostovtsev, V.V., Green, L.G., Fokin, V.V., and Sharpless, K.B., Angew. Chem., Int. Ed. Engl., 2002, vol. 41, pp. 2596–2599.

    Article  CAS  Google Scholar 

  8. Himo, F., Lovell, T., Hilgraf, R., Rostovtsev, V.V., Noodleman, L., Sharpless, K.B., and Fokin, V.V., J. Am. Chem. Soc., 2005, vol. 127, pp. 210–216.

    Article  CAS  PubMed  Google Scholar 

  9. Rodionov, V.O., Fokin, V.V., and Finn, M.G., Angew. Chem., Int. Ed. Engl., 2005, vol. 44, pp. 2210–2215.

    Article  CAS  Google Scholar 

  10. Straub, B.F., Chem. Commun., 2007, pp. 3868–3870.

  11. Ahlquist, M. and Fokin, V.V., Organometallics, 2007, vol. 26, pp. 4389–4390.

    Article  CAS  Google Scholar 

  12. Hein, J.E., Tripp, J.C., Krasnova, L.B., Sharpless, K.B., and Fokin, V.V., Angew. Chem., Int. Ed. Engl., 2009, vol. 48, pp. 8018–8021.

    Article  CAS  Google Scholar 

  13. Wang, Q., Chan, T.R., Hilgraf, R., Fokin, V.V., Sharpless, K.B., and Finn, M.G., J. Am. Chem. Soc., 2003, vol. 125, pp. 3192–3193.

    Article  CAS  PubMed  Google Scholar 

  14. Chan, T.R., Hilgraf, R., Sharpless, K.B., and Fokin, V.V., Org. Lett., 2004, vol. 6, pp. 2853–2855.

    Article  CAS  PubMed  Google Scholar 

  15. Lewis, W.G., Magallon, F.G., Fokin, V.V., and Finn, M.G., J. Am. Chem. Soc., 2004, vol. 126, pp. 9152–9153.

    Article  CAS  PubMed  Google Scholar 

  16. Gupta, S.S., Kuzelka, J., Singh, P., Lewis, W.G., Manchester, M., and Finn, M.G., Bioconjugate Chem., 2005, vol. 16, pp. 1572–1579.

    Article  CAS  Google Scholar 

  17. Rodionov, V.O., Presolski, S.I., Gardinier, S., Lim, Y.-H., and Finn, M.G., J. Am. Chem. Soc., 2007, vol. 129, pp. 12696–12704.

    Article  CAS  PubMed  Google Scholar 

  18. Rodionov, V.O., Presolski, S.I., Diaz, D.D., Fokin, V.V., and Finn, M.G., J. Am. Chem. Soc., 2007, vol. 129, pp. 12705–12712.

    Article  CAS  PubMed  Google Scholar 

  19. Baron, A., Blériot, Y., Sollogoub, M., and Vauzeilles, B., Org. Biomol. Chem., 2008, vol. 6, pp. 1898–1901.

    Article  CAS  PubMed  Google Scholar 

  20. Bergbreiter, D.E., Hamilton, P.N., and Koshti, N.M., J. Am. Chem. Soc., 2007, vol. 129, pp. 10666–10667.

    Article  CAS  PubMed  Google Scholar 

  21. Candelon, N., Lastécoueres, D., Diallo, A.K., Aranzaes, J.R., Astruc, D., and Vincent, J.-M., Chem. Commun., 2008, pp. 741–743.

  22. Akimova, G.S., Chistokletov, V.N., and Petrov, A.A., Zh. Org. Khim., 1965, vol. 1, pp. 2077–2078.

    CAS  Google Scholar 

  23. Akimova, G.S., Chistokletov, V.N., and Petrov, A.A., Zh. Org. Khim., 1967, vol. 3, pp. 968–974.

    CAS  Google Scholar 

  24. Akimova, G.S., Chistokletov, V.N., and Petrov, A.A., Zh. Org. Khim., 1967, vol. 3, pp. 2241–2247.

    CAS  Google Scholar 

  25. Akimova, G.S., Chistokletov, V.N., and Petrov, A.A., Zh. Org. Khim., 1968, vol. 4, pp. 389–394.

    CAS  Google Scholar 

  26. Krasiński, A., Fokin, V.V., and Sharpless, K.B., Org. Lett., 2004, vol. 6, pp. 1237–1240.

    Article  PubMed  CAS  Google Scholar 

  27. Zhang, L., Chen, X., Xue, P., Sun, H.H.Y., Williams, I.D., Sharpless, K.B., Fokin, V.V., and Jia, G., J. Am. Chem. Soc., 2005, vol. 127, pp. 15998–15999.

    Article  CAS  PubMed  Google Scholar 

  28. Rasmussen, L.K., Boren, B.C., and Fokin, V.V., Org. Lett., 2007, vol. 9, pp. 5337–5339.

    Article  CAS  PubMed  Google Scholar 

  29. Boren, B.C., Narayan, S., Rasmussen, L.K., Zhang, L., Zhao, H., Lin, Z., Jia, G., and Fokin, V.V., J. Am. Chem. Soc., 2008, vol. 130, pp. 8923–8930.

    Article  CAS  PubMed  Google Scholar 

  30. Kolb, H.C. and Sharpless, K.B., Drug Discov. Today, 2003, vol. 8, pp. 1128–1137.

    Article  CAS  PubMed  Google Scholar 

  31. Wang, Q., Chittaboina, S., and Barnhill, H.N., Lett. Org. Chem., 2005, vol. 2, pp. 293–301.

    Article  CAS  Google Scholar 

  32. Hawker, C.J. and Wooley, K.L., Science, 2005, vol. 309, pp. 1200–1205.

    Article  CAS  PubMed  Google Scholar 

  33. Binder, W.H. and Kluger, C., Curr. Org. Chem., 2006, vol. 10, pp. 1791–1815.

    Article  CAS  Google Scholar 

  34. Bock, V.D., Hiemstra, H., and van Maarseveen, J.H., Eur. J. Org. Chem., 2006, pp. 51–68.

  35. Santoyo-Gonzalez, F. and Hernandez-Mateo, F., Top. Heterocycl. Chem., 2007, vol. 7, pp. 133–177.

    Article  CAS  Google Scholar 

  36. Wu, P. and Fokin, V.V., Aldrichimica Acta, 2007, vol. 40, pp. 7–17.

    CAS  Google Scholar 

  37. Jean-François, L., Angew. Chem., Int. Ed. Engl., 2007, vol. 46, pp. 1018–1025.

    Article  CAS  Google Scholar 

  38. Wolfbeis, O.S., Angew. Chem., Int. Ed. Engl., 2007, vol. 46, pp. 2980–2982.

    Article  CAS  Google Scholar 

  39. Fokin, V.V., ACS Chem. Biol., 2007, vol. 2, pp. 775–778.

    Article  CAS  PubMed  Google Scholar 

  40. Evans, R.A., Aust. J. Chem., 2007, vol. 60, pp. 384–395.

    Article  CAS  Google Scholar 

  41. Nandivada, H., Jiang, X., and Lahann, J., Adv. Mater., 2007, vol. 19, pp. 2197–2208.

    Article  CAS  Google Scholar 

  42. Aprahamian, I., Miljanić, O.S., Dichtel, W.R., Isoda, K., Yasuda, T., Kato, T., and Stoddart, J.F., Bull. Chem. Soc. Jpn., 2007, vol. 80, pp. 1856–1869.

    Article  CAS  Google Scholar 

  43. Dondoni, A., Chem. Asian J, 2007, vol. 2, pp. 700–708.

    Article  CAS  PubMed  Google Scholar 

  44. Moses, J.E. and Moorhouse, A.D., Chem. Soc. Rev., 2007, vol. 36, pp. 1249–1262.

    Article  CAS  PubMed  Google Scholar 

  45. Fournier, D., Hoogenboom, R., and Schubert, U.S., Chem. Soc. Rev., 2007, vol. 36, pp. 1369–1380.

    Article  CAS  PubMed  Google Scholar 

  46. Angell, Y.L. and Burgess, K., Chem. Soc. Rev., 2007, vol. 36, pp. 1674–1689.

    Article  CAS  PubMed  Google Scholar 

  47. Binder, W.H. and Sachsenhofer, R., Macromol. Rapid Commun., 2007, vol. 28, pp. 15–54.

    Article  CAS  Google Scholar 

  48. Dedola, S., Nepogodieva, S.A., and Field, R.A., Org. Biomol. Chem., 2007, vol. 5, pp. 1006–1017.

    Article  CAS  PubMed  Google Scholar 

  49. Gil, M.V., Arévalo, M.J., and López, Ó., Synthesis, 2007, pp. 1589–1620.

  50. Dirks, A.J., Cornelissen, J.J.L.M., van Delft, F.L., van Herst, J.C.M., Nolte, R.J.M., Rowan, A.E., and Rutjes, F.P.J.T., QSAR Comb. Sci,. 2007, vol. 26, pp. 1200–1210.

    Article  CAS  Google Scholar 

  51. Lutz, J.-F. and Zarafshani, Z., Adv. Drug Deliv. Rev., 2008, vol. 60, pp. 958–970.

    Article  CAS  PubMed  Google Scholar 

  52. Meldal, M. and Tornøe, C.W., Chem. Rev., 2008, vol. 108, pp. 2952–3015.

    Article  CAS  PubMed  Google Scholar 

  53. Meldal, M., Macromol. Rapid Commun., 2008, vol. 29, pp. 1016–1051.

    Article  CAS  Google Scholar 

  54. Johnson, J.A., Finn, M.G., Koberstein, J.T., and Turro, N.J., Macromol. Rapid Commun., 2008, vol. 29, pp. 1052–1072.

    Article  CAS  Google Scholar 

  55. Droumaguet, B.L. and Velonia, K., Macromol. Rapid Commun., 2008, vol. 29, pp. 1073–1089.

    Article  CAS  Google Scholar 

  56. Binder, W.H. and Sachsenhofer, R., Macromol. Rapid Commun., 2008, vol. 29, pp. 952–981.

    Article  CAS  Google Scholar 

  57. Tron, G.C., Pirali, T., Billington, R.A., Canonico, P.L., Sorba, G., and Genazzani, A.A., Med. Res. Rev., 2008, vol. 28, pp. 278–308.

    Article  CAS  PubMed  Google Scholar 

  58. Lutz, J.-F. and Börner, H.G., Prog. Polym. Sci., 2008, vol. 33, pp. 1–39.

    Article  CAS  Google Scholar 

  59. Hein, C.D., Liu, X.-M., and Wang, D., Pharm. Res., 2008, vol. 25, pp. 2216–2230.

    Article  CAS  PubMed  Google Scholar 

  60. Bräse, S., Friedrich, A., Gartner, M., and Schröder, T., Top. Heterocycl. Chem., 2008, vol. 12, pp. 45–115.

    Article  CAS  Google Scholar 

  61. Sletten, E.M. and Bertozzi, C.R., Angew. Chem., Int. Ed. Engl., 2009, vol. 48, pp. 6974–6998.

    Article  CAS  Google Scholar 

  62. Best, M.D., Biochemistry, 2009, vol. 48, pp. 6571–6584.

    Article  CAS  PubMed  Google Scholar 

  63. van Dijk, M., Rijkers, D.T.S., Liskamp, R.M.J., van Nostrum, C.F., and Hennink, W.E., Bioconjugate Chem., 2009, vol. 20, pp. 2001–2016.

    Article  CAS  Google Scholar 

  64. Iha, R.K., Wooley, K.L., Nyström, A.M., Burke, D.J., Kade, M.J., and Hawker, C.J., Chem. Rev., 2009, vol. 109, pp. 5620–5686.

    Article  CAS  PubMed  Google Scholar 

  65. Click Chemistry for Biotechnology and Material Science, Lahann, J., Ed., Chichester: Wiley, 2009.

    Google Scholar 

  66. Schilling, C., Jung, N., and Bräse, S., in Organic Azides: Syntheses and Applications, Brase, S. and Banert, K., Eds., Chichester: Wiley, 2010, pp. 269–284.

    Google Scholar 

  67. Tornøe, C.W. and Meldal, M., in Organic Azides: Syntheses and Applications, Brase, S. and Banert, K., Eds., Chichester: Wiley, 2010, pp. 285–310.

    Google Scholar 

  68. Sumerlin, B.S. and Vogt, A.P., Macromolecules, 2010, vol. 43, pp. 1–13.

    Article  CAS  Google Scholar 

  69. Hermanson, G.T., Bioconjugate Techniques. 2nd Ed., San Diego: Academic, 2008.

    Google Scholar 

  70. Gramlich, P.M.E., Wirges, C.T., Manetto, A., and Carell, T., Angew. Chem., Int. Ed. Engl., 2008, vol. 47, pp. 8350–8358.

    Article  CAS  Google Scholar 

  71. Amblard, F., Cho, J.H., and Schinazi, R.F., Chem. Rev., 2009, vol. 109, pp. 4207–4220.

    Article  CAS  PubMed  Google Scholar 

  72. Seo, T.S., Li, Z., Ruparel, H., and Ju, J., J. Org. Chem., 2003, vol. 68, pp. 609–612.

    Article  CAS  PubMed  Google Scholar 

  73. Li, Z., Seo, T.S., and Ju, J., Tetrahedron Lett., 2004, vol. 45, pp. 3143–3146.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  75. Gololobov, Y.G., Zhmurova, I.N., and Kasukhin, L.F., Tetrahedron, 1981, vol. 37, pp. 437–472.

    Article  CAS  Google Scholar 

  76. Meier, C. and Huynh-Dinha, T., Bioorg. Med. Chem. Lett., 1991, vol. 1, pp. 527–530.

    Article  CAS  Google Scholar 

  77. Jawalekar, A.M., Meeuwenoord, N., Cremers, J.(S.)G.O., Overkleef H.S., van der Marel, G.A., Rutjes, F.P.J.T., and van Delft, F.L., J. Org. Chem., 2008, vol. 73, pp. 287–290.

    Article  CAS  PubMed  Google Scholar 

  78. Polushin, N.N., Smirnov, I.P., Verentchikov, A.N., and Coull, J.M., Tetrahedron Lett., 1996, vol. 19, pp. 3227–3230.

    Article  Google Scholar 

  79. El-Sagheer, A. and Brown, T., J. Am. Chem. Soc., 2009, vol. 131, pp. 3958–3964.

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  81. Efimov, V.A., Aralov, A.V., Fedunin, S.V., Klykov, V.N., and Chakhmakhcheva, O.G., Bioorg. Khim., 2009, vol. 35, pp. 270–273 [Russ. J. Bioorg. Chem., 2009, vol. 35, pp. 250–253].

    CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  83. Esipov, D.S., Esipova, O.V., and Korobko, V.G., Nucleosides Nucleotides, 1998, vol. 17, pp. 1697–1704.

    Article  CAS  Google Scholar 

  84. Ötvös, L., Bajor, Z., Kraicsovits, F., Sági, G., and Tegyey, S., Nucleosides Nucleotides Nucleic Acids, 2002, vol. 21, pp. 79–92.

    Article  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  86. Kiviniemi, A., Virta, P., and Lönnberg, H., Bioconjugate Chem., 2008, vol. 19, pp. 1726–1734.

    Article  CAS  Google Scholar 

  87. Pourceau, G., Meyer, A., Vasseur, J.-J., and Morvan, F., J. Org. Chem., 2009, vol. 74, pp. 6837–3842.

    Article  CAS  PubMed  Google Scholar 

  88. Jentzsch, E. and Mokhir, A., Inorg. Chem., 2009, vol. 48, pp. 9593–9595.

    Article  CAS  PubMed  Google Scholar 

  89. Shchepinov, M.S. and Stetsenko, D.A., Bioorg. Med. Chem. Lett., 1997, vol. 9, pp. 1181–1184.

    Article  Google Scholar 

  90. Miller, G.P. and Kool, E.T., J. Org. Chem., 2004, vol. 69, pp. 2404–2410.

    Article  CAS  PubMed  Google Scholar 

  91. Miller, G.P. and Kool, E.T., Org. Lett., 2002, vol. 4, pp. 3599–3601.

    Article  CAS  PubMed  Google Scholar 

  92. Xu, Y. and Kool, E.T., Tetrahedron Lett., 1997, vol. 32, pp. 5595–5598.

    Article  Google Scholar 

  93. Alvira, M. and Eritja, R., Chem. Biodiv, 2007, vol. 4, pp. 2798–2809.

    Article  CAS  Google Scholar 

  94. Lietard, J., Meyer, A., Vasseur, J.-J., and Morvan, F., Tetrahedron Lett., 2007, vol. 48, pp. 8795–8798.

    Article  CAS  Google Scholar 

  95. Lietard, J., Meyer, A., Vasseur, J.-J., and Morvan, F., J. Org. Chem., 2008, vol. 73, pp. 191–200.

    Article  CAS  PubMed  Google Scholar 

  96. Nakane, M., Ichikawa, S., and Matsuda, A., J. Org. Chem., 2008, vol. 73, pp. 1842–1851.

    Article  CAS  PubMed  Google Scholar 

  97. Pourceau, G., Meyer, A., Vasseur, J.-J., and Morvan, F., J. Org. Chem., 2009, vol. 74, pp. 1218–1222.

    Article  CAS  PubMed  Google Scholar 

  98. Pourceau, G., Meyer, A., Vasseur, J.-J., and Morvan, F., Curr. Prot. Nucl. Acid Chem., 2009, p. 25.

  99. Wu, X. and Pitsch, S., Bioconjugate Chem., 1999, vol. 10, pp. 921–924.

    Article  CAS  Google Scholar 

  100. Wu, X. and Pitsch, S., Helv. Chim. Acta, 2000, vol. 83, pp. 1127–1144.

    Article  CAS  Google Scholar 

  101. Grajkowski, A., Cies’lak, J., Kauffman, J.S., Duff, R.J., Norris, S., Freedberg, D.I., and Beaucage, S.L., Bioconjugate Chem., 2008, vol. 19, pp. 1696–1706.

    Article  CAS  Google Scholar 

  102. Zhang, J., Pourceau, G., Meyer, A., Vidal, S., Praly, J.-P., Souteyrand, E., Vasseur, J.-J., Morvan, F., and Chevolot, Y., Biosens. Bioelectron., 2009, vol. 24, pp. 2515–2521.

    Article  CAS  PubMed  Google Scholar 

  103. Ouyang, X., Shestopalov, I.A., Sinha, S., Zheng, G., Pitt, C.L.W., Li, W.-H., Olson, A.J., and Chen, J.K., J. Am. Chem. Soc., 2009, vol. 131, pp. 13255–13269.

    Article  CAS  PubMed  Google Scholar 

  104. Kanan, M.W., Rozenman, M.M., Sakurai, K., Snyder, T.M., and Liu, D.R., Nature, 2004, vol. 431, pp. 545–549.

    Article  CAS  PubMed  Google Scholar 

  105. Kumar, R., El-Sagheer, A., Tumpane, J., Lincoln, P., Wilhelmsson, L.M., and Brown, T., J. Am. Chem. Soc., 2007, vol. 129, pp. 6859–6864.

    Article  CAS  PubMed  Google Scholar 

  106. El-Sagheer, A. and Brown, T., Curr. Prot. Nucl. Acid Chem., 2008, p. 21.

  107. El-Sagheer, A.H., Kumar, R., Findlow, S., Werner, J.M., Lane, A.N., and Brown, T., ChemBioChem, 2008, vol. 9, pp. 50–52.

    Article  CAS  PubMed  Google Scholar 

  108. Nordell, P., Westerlund, F., Reymar, A., El-Sagheer, A., Brown, T., Norden, B., and Lincoln, P., J. Am. Chem. Soc., 2008, vol. 130, pp. 14651–14658.

    Article  CAS  PubMed  Google Scholar 

  109. Kocalka, P., El-Sagheer, A., and Brown, T., ChemBioChem, 2008, vol. 9, pp. 1280–1285.

    Article  CAS  PubMed  Google Scholar 

  110. Rozenman, M.M., Kanan, M.W., and Liu, D.R., J. Am. Chem. Soc., 2007, vol. 129, pp. 14933–14938.

    Article  CAS  PubMed  Google Scholar 

  111. El-Sagheer, A.H., Nucleosides Nucleotides Nucleic Acids, 2009, vol. 28, pp. 315–323.

    Article  CAS  PubMed  Google Scholar 

  112. Gorin, D.J., Kamlet, A.S., and Liu, D.R., J. Am. Chem. Soc., 2009, vol. 131, pp. 9189–9191.

    Article  CAS  PubMed  Google Scholar 

  113. Wang, C.-Y., Seo, T.S., Li, Z., Ruparel, H., and Ju, J., Bioconjugate Chem., 2003, vol. 14, pp. 697–701.

    Article  CAS  Google Scholar 

  114. Seo, T.S., Bai, X., Ruparel, H., Li, Z., Turro, N.J., and Ju, J., Proc. Natl. Acad. Sci. USA, 2004, vol. 101, pp. 5488–5493.

    Article  CAS  PubMed  Google Scholar 

  115. Seo, T.S., Bai, X., Kim, D.H., Meng, Q., Shi, S., Ruparel, H., Li, Z., Turro, N.J., and Ju, J., Proc. Natl. Acad. Sci. USA, 2005, vol. 102, pp. 5926–5931.

    Article  CAS  PubMed  Google Scholar 

  116. Inkster, J.A.H., Adam, M.J., Storr, T., and Ruth, T.J., Nucleosides Nucleotides Nucleic Acids, 2009, vol. 28, pp. 1131–1143.

    Article  CAS  PubMed  Google Scholar 

  117. Humenik, M., Huang, Y., Wang, Y., and Sprinzl, M., ChemBioChem, 2007, vol. 8, pp. 1103–1106.

    Article  CAS  PubMed  Google Scholar 

  118. Chen, L., Rengifo, H.R., Grigoras, C., Li, X., Li, Z., Ju, J., and Koberstein, J.T., Biomacromolecules, 2008, vol. 9, pp. 2345–2352.

    Article  CAS  PubMed  Google Scholar 

  119. Xu, Y., Suzuki, Y., and Komiyama, M., Angew. Chem., Int. Ed. Engl., 2009, vol. 48, pp. 3281–3284.

    Article  CAS  Google Scholar 

  120. Alemán, E.A., Pedini, H.S., and Rueda, D., ChemBioChem, 2009, vol. 10, pp. 2862–2866.

    Article  PubMed  CAS  Google Scholar 

  121. Chao, J., Huang, W.-Y., Wang, J., Xiao, S.-J., Tang, Y.-C., and Liu, J.-N., Biomacromolecules, 2009, vol. 10, pp. 877–883.

    Article  CAS  PubMed  Google Scholar 

  122. Gartner, Z.J., Grubina, R., Calderone, C.T., and Liu, D.R., Angew. Chem., Int. Ed. Engl., 2003, vol. 42, pp. 1370–1375.

    Article  CAS  Google Scholar 

  123. Jacobsen, M.F., Ravnsbæk, J.B., and Gothelf, K.V., Org. Biomol. Chem., 2010, vol. 8, pp. 50–52.

    Article  CAS  PubMed  Google Scholar 

  124. Gibson, K.J. and Benkovic, S.E., Nucleic Acid Res., 1987, vol. 15, pp. 6455–6467.

    Article  CAS  PubMed  Google Scholar 

  125. Podkowinski, J. and Gornicki, P., Nucleic Acid Res., 1991, vol. 19, pp. 801–808.

    Article  CAS  PubMed  Google Scholar 

  126. Muralikrishna, P. and Cooperman, B., Biochemistry, 1991, vol. 30, pp. 5421–5428.

    Article  CAS  PubMed  Google Scholar 

  127. Capson, T.L., Benkovic, S.E., and Nossal, N.G., Cell, 1991, vol. 65, pp. 249–258.

    Article  CAS  PubMed  Google Scholar 

  128. Dobrikov, M.I., Zarytova, V.F., Komarova, N.I., Levina, A.S., Lokhov, S.A., Prikhod’ko, T.A., Shishkin, G.V., Tabatadze, D.R., and Zaalishvili, M.M., Bioorg. Khim., 1992, vol. 18, pp. 540–549.

    CAS  PubMed  Google Scholar 

  129. Mitchell, P., Stade, K., Oßwald, M., and Brimacombe R., Nucleic Acid Res., 1993, vol. 21, pp. 887–896.

    Article  CAS  PubMed  Google Scholar 

  130. Oh, B.-K. and Pacel, N.R., Nucleic Acids Res., 1994. vol. 22. pp. 4087–4094.

    Article  CAS  PubMed  Google Scholar 

  131. Muralikrishna, P. and Cooperman, B.S., Biochemistry, 1994, vol. 33, pp. 1392–1398.

    Article  CAS  PubMed  Google Scholar 

  132. Mullen, M.A., Wang, H., Wilcox, K., and Herman, T., DNA Cell Biol., 1994, vol. 13, pp. 521–530.

    Article  CAS  PubMed  Google Scholar 

  133. Kazantsev, A.V., Maksakova, G.A., and Fedorova, O.S., Bioorg. Khim., 1995, vol. 21, pp. 767–773.

    CAS  PubMed  Google Scholar 

  134. Godovikova, T.S., Berezovskii, M.V., and Knorre, D.G., Bioorg. Khim., 1995, vol. 21, pp. 858–867.

    CAS  PubMed  Google Scholar 

  135. Capson, T.L., Benkovic, S.J., and Nossal, N.G., Methods Enzymol., 1995, vol. 262, pp. 449–456.

    Article  CAS  PubMed  Google Scholar 

  136. Babaylova, E., Graifer, D., Malygin, A., Stahl, J., Shatsky, I., and Karpova, G., Nucleic Acid Res., 2009, vol. 37, pp. 1141–1151.

    Article  CAS  PubMed  Google Scholar 

  137. Towbin, H. and Elson, D., Nucleic Acid Res., 1978, vol. 5, pp. 3389–3407.

    Article  CAS  PubMed  Google Scholar 

  138. Dobrikov, M.I., Gaidamakov, S.A., Gainutdinov, T.I., Koshkin, A.A., and Vlassov, V.V., Antisense Nucl. Acids Drug Dev., 1997, vol. 7, pp. 309–317.

    CAS  Google Scholar 

  139. Dobrikov, M.I., Gaidamakov, S.A., Gainutdinov, T.I., Ivanova, T.M., and Vlasov, V.V., Bioorg. Khim., 1999, vol. 25, pp. 137–146.

    CAS  PubMed  Google Scholar 

  140. Dobrikov, M.I., Gainutdinov, T.I., Ivanova, T.I., and Vlassov, V.V., Bioorg. Khim., 2000, vol. 26, pp. 617–622 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2000, vol. 26, pp. 553–558].

    CAS  PubMed  Google Scholar 

  141. Gainutdinov, T.I., Shestova, O.E., Yakubov, L.A., Dobrikov, M.I., and Vlassov, V.V., Izv. Akad. Nauk, Ser. Khim., 2002, vol. 51, pp. 1108–1112 [Russ. Chem. Bull. (Eng. Transl.), 2002, vol. 51, pp. 1198–1203].

    Google Scholar 

  142. Duca, M., Guianvarc’h, D., Oussedik, K., Halby, L., Garbesi, A., Dauzonne, D., Monneret, C., Osheroff, N., Giovannangeli, C., and Arimondo, P.B., Nucleic Acid Res., 2006, vol. 34, pp. 1900–1911.

    Article  CAS  PubMed  Google Scholar 

  143. Liu, J., Fan, Q.R., Sodeoka, M., Lane, W.S., and Verdine, G.L., Chem. Biol, 1994, vol. 1, pp. 47–55.

    Article  CAS  PubMed  Google Scholar 

  144. Weisbrod, S.H. and Marx, A., Chem. Commun., 2008, pp. 5675–5685.

  145. Weisbrod, S.H., Baccaro, A., and Marx, A., Nucleic Acids Symp. Ser., 2008, vol. 52, pp. 383–384.

    Article  CAS  Google Scholar 

  146. Baccaro, A., Weisbrod, S.H., and Marx, A., Synthesis, 2007, pp. 1949–1954.

  147. Gierlich, J., Gutsmiedl, K., Gramlich, P.M.E., Schmidt, A., Burley, G.A., and Carell, T., Chem. Eur. J., 2007, vol. 13, pp. 9486–9494.

    Article  CAS  Google Scholar 

  148. Prober, J.M., Trainor, G.L., Dam, R.J., Hobbs, F.W., Robertson, C.W., Zagursky, R.J., Cocuzza, A.J., Jensen, M.A., and Baumeister, K., Science, 2007, vol. 238, pp. 336–341.

    Article  Google Scholar 

  149. Confalone, P.N., J. Heterocycl. Chem., 1990, vol. 27, pp. 31–46.

    Article  CAS  Google Scholar 

  150. Heidenreich, O., Kruhøffer, M., Grosse, F., and Eckstein, F., Eur. J. Biochem., 1990, vol. 192, pp. 621–625.

    Article  CAS  PubMed  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  153. Guo, J., Xu, N., Li, Z., Zhang, S., Wu, J., Kim, D.H., Marma, M.S., Meng, Q., Cao, H., Li, X., Shi, S., Yu, L., Kalachikov, S., Russo, J.J., Turro, N.J., and Ju, J., Proc. Natl. Acad. Sci. USA, 2008, vol. 105, pp. 9145–9150.

    Article  CAS  PubMed  Google Scholar 

  154. Bentley, D.R., Balasubramanian, S., Swerdlow, H.P., Smith, G.P., Milton, J., Brown, C.G., Hall, K.P., Evers, D.J., Barnes, C.L., Bignell, H.R., et al., (>100 co-authors), Nature, 2008, vol. 456, pp. 53–59.

    Article  CAS  PubMed  Google Scholar 

  155. Milton, J., Wu, X., Smith, M., Brennan, J., Barnes, C., Liu, X., and Ruediger, S., WO Patent no. 018 487, 2004.

  156. Milton, J. and Liu, X., US Patent no. 7 592 435, 2009.

  157. Comstock, L.R. and Rajski, S.R., Nucleic Acid Res., 2005, vol. 33, pp. 1644–1652.

    Article  CAS  PubMed  Google Scholar 

  158. Comstock, L.R. and Rajski, S.R., J. Am. Chem. Soc., 2005, vol. 127, pp. 14136–14137.

    Article  CAS  PubMed  Google Scholar 

  159. Evans, R.K., Johnson, J.D., and Haley, B.E., Proc. Natl. Acad. Sci. USA, 2005, vol. 83, pp. 5382–5386.

    Article  Google Scholar 

  160. Evans, R.K. and Haley, B.E., Biochemistry, 1987, vol. 26, pp. 269–276.

    Article  CAS  PubMed  Google Scholar 

  161. Lee, D.K., Evans, R.K., Blanco, J., Gottesfeld, J., and Johnson, J.D., J. Biol. Chem., 1991, vol. 266, pp. 16478–16484.

    CAS  PubMed  Google Scholar 

  162. Woody, A.-Y.M., Evans, R.K., and Woody, W.W., Biochem. Biophys. Res. Commun., 1988, vol. 150, pp. 917–924.

    Article  CAS  PubMed  Google Scholar 

  163. Meffert, R. and Dose, K., FEBS Lett., 1988, vol. 239, pp. 190–194.

    Article  CAS  PubMed  Google Scholar 

  164. Meffert, R., Rathgeber, G., Schäfer, H.-J., and Dose, K., Nucleic Acid Res., 1990, vol. 18, pp. 6633–6636.

    Article  CAS  PubMed  Google Scholar 

  165. Ettner, N., Haak, U., Niederweis, M., and Hillen, W., Nucleosides Nucleotides, 1993, vol. 12, pp. 757–771.

    Article  CAS  Google Scholar 

  166. Hanna, M.M., Dissinger, S., Williams, B.D., and Colston, J.E., Biochemistry, 1989, vol. 28, pp. 5814–5820.

    Article  CAS  PubMed  Google Scholar 

  167. Dissinger, S. and Hanna, M.M., J. Mol. Biol., 1991, vol. 219, pp. 11–25.

    Article  CAS  PubMed  Google Scholar 

  168. Hanna, M.M., Zhang, Y., Reidling, J.C., Thomas, M.J., and Jou, J., Nucleic Acid Res., 1993, vol. 21, pp. 2073–2079.

    Article  CAS  PubMed  Google Scholar 

  169. Bartholomew, B., Kassavetis, G.A., Braun, B.R., and Geiduschek, E.P., EMBO J., 1990, vol. 9, pp. 2197–2205.

    CAS  PubMed  Google Scholar 

  170. Bartholomew, B., Tinker, R.L., Kassavetis, G.A., and Geiduschek, E.P., Methods Enzymol., 1995, vol. 262, pp. 476–494.

    Article  CAS  PubMed  Google Scholar 

  171. Wlassoff, W.A., Dobrikov, M.I., Safronov, I.V., Dudko, R.Y., Bogachev, V.S., Kandaurova, V.V., Shishkin, G.V., Dymshits, G.M., and Lavrik, O.I., Bioconjugate Chem., 1995, vol. 6, pp. 352–360.

    Article  CAS  Google Scholar 

  172. Lavrik, O.I., Nasheuer, H.-P., Weisshart, K., Wold, M.S., Prasad, R., Beard, W.A., Wilson, S.H., and Favre, A., Nucleic Acid Res., 1998, vol. 26, pp. 602–607.

    Article  CAS  PubMed  Google Scholar 

  173. Kolpashchikov, D.M., Alexandrova, L.A., Zakirova, N.F., Khodureva, S.N., and Lavrik, O.I., Bioorg. Khim., 2000, vol. 26, pp. 151–155 [Russ. J. Bioorg. Chem. (Eng. Transl.), 2000, vol. 26, pp. 134–137].

    CAS  PubMed  Google Scholar 

  174. Kolpashchikov, D.M., Ivanova, T.M., Boghachev, V.S., Nasheuer, H.-P., Weisshart, K., Favre, A., Pestryakov, P.E., and Lavrik, O.I., Bioconjugate Chem., 2000, vol. 11, pp. 445–451.

    Article  CAS  Google Scholar 

  175. Safronov, I.V., Shcherbik, N.V., Khodyreva, S.N., Vlasov, V.A., Dobrikov, M.I., Shishkin, G.V., and Lavrik, O.I., Bioorg. Khim., 1997, vol. 23, pp. 576–585.

    CAS  PubMed  Google Scholar 

  176. Lavrik, O.I., Prasad, R., Sobol, R.W., Horton, J.K., Ackerman, E.J., and Wilson, S.H., J. Biol. Chem., 2001, vol. 276, pp. 25541–25548.

    Article  CAS  PubMed  Google Scholar 

  177. Drachkova, I.A., Petruseva, I.O., Safronov, I.V., Zakharenko, A.L., Shishkin, G.V., Lavrik, O.I., and Khodyreva, S.N., Bioorg. Khim., 2001, vol. 27, pp. 197–204 [Russ. J. Bioorg. Chem. (Eng. Transl.), 2001, vol. 27, pp. 173–179].

    CAS  PubMed  Google Scholar 

  178. Safronov, I.V., Drachkova, I.A., Petruseva, I.O., Khodyreva, S.N., Dobrikov, M.I., Ivanova, T.I., Shishkin, G.V., and Lavrik, O.I., Bioorg. Khim., 2001, vol. 27, pp. 372–382 [Russ. J. Bioorg. Chem. (Eng. Transl.), 2001, vol. 27, pp. 330–339].

    CAS  PubMed  Google Scholar 

  179. Dezhurov, S.V., Grin, I.R., Safronov, I.V., Shishkin, G.V., Lavrik, O.I., and Khodyreva, S.N., Russ. Chem. Bull., 2005, vol. 54, pp. 1311–1321.

    Article  CAS  Google Scholar 

  180. Dezhurov, S.V., Khodyreva, S.N., Plekhanova, E.S., and Lavrik, O.I., Bioconjugate Chem., 2005, vol. 16, pp. 215–222.

    Article  CAS  Google Scholar 

  181. Dyrkheeva, N.S., Khodyreva, S.N., and Lavrik, O.I., Bioorg. Khim., 2008, vol. 34, pp. 372–382 Russ. J. Bioorg. Chem. (Eng. Transl.), 2008, vol. 34, pp. 192–200].

    Google Scholar 

  182. Belousova, E.A., Crespan, E., Lebedeva, N.A., Rechkunova, N.J., Hübscher, U., Maga, G., and Lavrik, O.I., Med. Chem., 2008, vol. 4, pp. 155–162.

    Article  CAS  PubMed  Google Scholar 

  183. Khlimankov, D.Yu., Petruseva, I.O., Rechkunova, N.I., Belousova, E.A., Kolpashchikov, D.M., Khodyreva, S.N., and Lavrik, O.I., Bioorg. Khim., 2001, vol. 27, pp. 205–209 [Russ. J. Bioorg. Chem. (Eng. Transl.), 2001, vol. 27, pp. 180–183].

    PubMed  Google Scholar 

  184. Dezhurov, S.V., Khodyreva, S.N., Rechkunova, N.I., Kolpashchikov, D.M., and Lavrik, O.I., Bioorg. Khim., 2003, vol. 29, pp. 75–82 [Russ. J. Bioorg. Chem. (Eng. Transl.), 2003, vol. 29, pp. 66–72].

    CAS  PubMed  Google Scholar 

  185. Demeshkina, N.A., Laletina, E.S., Meschaninova, M.I., Repkova, M.N., Ven’yaminova, A.G., Graifer, D.M., and Karpova, G.G., Molecular Biology, 2003, vol. 37, pp. 132–139.

    Article  CAS  Google Scholar 

  186. Lebedeva, N.A., Rechkunova, N.I., Dezhurov, S.V., Degtyarev, S.Kh., and Lavrik, O.I., Bioorg. Khim., 2004, vol. 30, pp. 369–374 [Russ. J. Bioorg. Chem., 2004, vol. 30, pp. 332–336].

    CAS  PubMed  Google Scholar 

  187. Khodyreva, S.N. and Lavrik, O.I., Curr. Med. Chem., 2005, vol. 12, pp. 641–655.

    CAS  PubMed  Google Scholar 

  188. Cañete, S.J.P., Yang, W., and Lai, R.Y., Chem. Commun., 2009, pp. 4835–4837.

  189. Chung, M., Lowe, R.D., Chan, Y.-H.M., Ganesan, P.V., and Boxer, S.G., J. Struct. Biol., 2009, vol. 168, pp. 190–199.

    Article  CAS  PubMed  Google Scholar 

  190. Erdem, S.S., Nesterova, I.V., Soper, S.A., and Hammer, R.P., J. Org. Chem., 2009, vol. 74, pp. 9280–9286.

    Article  CAS  PubMed  Google Scholar 

  191. Duckworth, B.P., Chen, Y., Wollack, J.W., Sham, Y., Mueller, J.D., Taton, T.A., and Distefano, M.D., Angew. Chem., Int. Ed. Engl., 2007, vol. 46, pp. 8819–8822.

    Article  CAS  Google Scholar 

  192. Singh, I., Vyle, J.S., and Heaney, F., Chem. Commun., 2009, pp. 3276–3278.

  193. Morvan, F., Meyer, A., Pourceau, G., Vidal, S., Chevolot, Y., Souteyrand, E., Vasseur, J.-J., Nucleic Acids Symp. Ser., 2008, vol. 52, pp. 47–48.

    Article  CAS  Google Scholar 

  194. Rozkiewicz, D.I., Gierlich, J., Burley, G.A., Gutsmiedl, K., Carell, T., Ravoo, B.J., and Reinhoudt, D.N., ChemBioChem, 2007, vol. 8, pp. 1997–2002.

    Article  CAS  PubMed  Google Scholar 

  195. Gramlich, P.M.E., Warncke, S., Gierlich, J., and Carell, T., Angew. Chem., Int. Ed. Engl., 2008, vol. 47, pp. 3442–3444.

    Article  CAS  Google Scholar 

  196. Berndl, S., Herzig, N., Kele, P., Lachmann, D., Li, X., Wolfbeis, O.S., and Wagenknecht, H.-A., Bioconjugate Chem., 2009, vol. 20, pp. 558–564.

    Article  CAS  Google Scholar 

  197. Ustinov, A.V., Dubnyakova, V.V., and Korshun, V.A., Nucleosides Nucleotides Nucleic Acids, 2007, vol. 26, pp. 751–754.

    Article  CAS  PubMed  Google Scholar 

  198. Ustinov, A.V., Dubnyakova, V.V., and Korshun, V.A., Tetrahedron, 2008, vol. 64, pp. 1467–1473.

    Article  CAS  Google Scholar 

  199. Pourceau, G., Meyer, A., Vasseur, J.J., and Morvan, F., J. Org. Chem., 2008, vol. 73, pp. 6014–6017.

    Article  CAS  PubMed  Google Scholar 

  200. Morvan, F., Meyer, A., Jochum, A., Sabin, C., Chevolot, Y., Imberty, A., Praly, J.-P., Vasseur, J.-J., Souteyrand, E., and Vidal, S., Bioconjugate Chem., 2007, vol. 18, pp. 1637–1643.

    Article  CAS  Google Scholar 

  201. Dioubankova, N.N., Malakhov, A.D., Stetsenko, D.A., Gait, M.J., and Korshun, V.A., Tetrahedron, 2006, vol. 62, pp. 6762–6773.

    Article  CAS  Google Scholar 

  202. Nakahara, M., Kuboyama, T., Izawa, A., Hari, Y., Imanishi, T., and Obika, S., Bioorg. Med. Chem. Lett., 2009, vol. 19, pp. 3316–3319.

    Article  CAS  PubMed  Google Scholar 

  203. Moni, L., Pourceau, G., Zhang, J., Meyer, A., Vidal, S., Souteyrand, E., Dondoni, A., Morvan, F., Chevolot, Y., Vasseur, J.-J., and Marra, A., ChemBioChem, 2009, vol. 10, pp. 1369–1378.

    Article  CAS  PubMed  Google Scholar 

  204. Kvach, M.V., Prokhorenko, I.A., Ustinov, A.V., Gontarev, S.V., Korshun, V.A., and Shmanai, V.V., Nucleosides Nucleotides Nucleic Acids, 2007, vol. 26, pp. 809–813.

    Article  CAS  PubMed  Google Scholar 

  205. Ustinov, A.V. and Korshun, V.A., Izv. Akad. Nauk, Ser. Khim., 2006, no. 6, pp. 1220–1226 [Russ. Chem. Bull. (Eng. Transl.), 2006, vol. 55, pp. 1268–1274.

  206. Géci, I., Filichev, V.V., and Pedersen, E.B., Bioconjugate Chem., 2006, vol. 17, pp. 950–957.

    Article  CAS  Google Scholar 

  207. Géci, I., Filichev, V.V., and Pedersen, E.B., Chem.-Eur. J., 2007, vol. 13, pp. 6379–6386.

    Article  CAS  Google Scholar 

  208. Grøtli, M., Douglas, M., Beijer, B., GarcÍa, R.G., Eritja, R., and Sproat, B., J. Chem. Soc., Perkin Trans., 1997, pp. 2779–2788.

  209. Grøtli, M., Douglas, M., Eritja, R., and Sproat, B., Tetrahedron, 1998, vol. 54, pp. 5899–5914.

    Article  Google Scholar 

  210. Korshun, V.A., Stetsenko, D.A., and Gait, M.J., J. Chem. Soc., Perkin Trans., 2002, pp. 1092–1104.

  211. Korshun, V.A., Stetsenko, D.A., and Gait, M.J., Current Prot. Nucleic Acids Chem., 2003, pp. 4.21.1–4.21.25.

  212. Buff, R. and Hunziker, J., Bioorg. Med. Chem. Lett., 1998, vol. 8, pp. 521–524.

    Article  CAS  PubMed  Google Scholar 

  213. Buff, R. and Hunziker, J., Synlett., 1999, pp. 905–908.

  214. Buff, R. and Hunziker, J., Nucleosides Nucleotides, 1999, vol. 18, pp. 1387–1388.

    Article  CAS  Google Scholar 

  215. Buff, R. and Hunziker, J., Helv. Chim. Acta, 2002, vol. 85, pp. 224–254.

    Article  CAS  Google Scholar 

  216. Nadler, A. and Diederichsen, U., Eur. J. Org. Chem., 2008, pp. 1544–1549.

  217. Hrdlicka, P.J., Kumar, T.S., and Wengel, J., Eur. J. Org. Chem., 2005, pp. 5184–5188.

  218. Gogoi, K., Mane, M.V., Kunte, S.S., and Kumar, V.A., Nucleic Acid Res., 2007, vol. 35, e139.

  219. Graham, D., Parkinson, J.A., and Brown, T., J. Chem. Soc., Perkin Trans., 1998, pp. 1131–1138.

  220. Gierlich, J., Burley, G.A., Gramlich, P.M.E., Hammond, D.M., and Carell, T., Org. Lett., 2006, vol. 8, pp. 3639–3642.

    Article  CAS  PubMed  Google Scholar 

  221. Gorodetsky, A.A., Green, O., Yavin, E., and Barton, J.K., Bioconjugate Chem., 2007, vol. 18, pp. 1434–1441.

    Article  CAS  Google Scholar 

  222. Seela, F. and Sirivolu, V.R., Chem. Biodiv., 2006, vol. 3, pp. 509–514.

    Article  CAS  Google Scholar 

  223. Seela, F. and Sirivolu, V.R., Nucleosides Nucleotides Nucleic Acids, 2007, vol. 26, pp. 597–601.

    Article  CAS  PubMed  Google Scholar 

  224. Seela, F. and Sirivolu, V.R., Helv. Chim. Acta, 2007, vol. 90, pp. 535–552.

    Article  CAS  Google Scholar 

  225. Seela, F., Sirivolu, V.R., and Chittepu, P., Bioconjugate Chem., 2008, vol. 19, pp. 211–224.

    Article  CAS  Google Scholar 

  226. Hammond, D.M., Manetto, A., Gierlich, J., Azov, V.A., Gramlich, P.M.E., Burley, G.A., Maul, M., and Carell, T., Angew. Chem., Int. Ed. Engl., 2007, vol. 46, pp. 4184–4187.

    Article  CAS  Google Scholar 

  227. Seela, F. and Ingale, S.A., J. Org. Chem., 2010, vol. 75, pp. 284–295.

    Article  CAS  PubMed  Google Scholar 

  228. Seela, F. and Ming, X., Helv. Chim. Acta, 2008, vol. 91, pp. 1181–1200.

    Article  CAS  Google Scholar 

  229. Ming, X., Leonard, P., Heindl, D., and Seela, F., Nucleic Acids Symp. Ser., 2008, vol. 52, pp. 471–472.

    Article  CAS  Google Scholar 

  230. Seela, F., Xiong, H., Leonard, P., and Budow, S., Org. Biomol. Chem., 2009, vol. 7, pp. 1374–1387.

    Article  CAS  PubMed  Google Scholar 

  231. Ami, T. and Fujimoto, K., ChemBioChem, 2008, vol. 9, pp. 2071–2074.

    Article  CAS  PubMed  Google Scholar 

  232. Ami, T., Yoshimura, Y., Matsuzaki, T., and Fujimoto, K., J. Photopolymer Sci. Tecnol., 2009, vol. 22, pp. 262–272.

    Google Scholar 

  233. Sirivolu, V.R., Chittepu, P., and Seela, F., ChemBioChem, 2008, vol. 9, pp. 2305–2316.

    Article  CAS  PubMed  Google Scholar 

  234. Freier, S.M. and Altmann, K.-H., Nucleic Acid Res., 1997, vol. 25, pp. 4429–4443.

    Article  CAS  PubMed  Google Scholar 

  235. Skorobogatyi, M.V., Malakhov, A.D., Pchelintseva, A.A., Turban, A.A., Bondarev, S.L., and Korshun, V.A., ChemBioChem, 2006, vol. 7, pp. 810–816.

    Article  CAS  PubMed  Google Scholar 

  236. Seela, F. and Sirivolu, V.R., Org. Biomol. Chem., 2008, vol. 6, pp. 1674–1687.

    Article  CAS  PubMed  Google Scholar 

  237. Woo, J., Meyer, R.B., and Gamper, H.B., Nucleic Acid Res., 1996, vol. 24, pp. 2470–2475.

    Article  CAS  PubMed  Google Scholar 

  238. Meyer, A., Bouillon, C., Vidal, S., Vasseura, J.-J., and Morvan, F., Tetrahedron Lett., 2006, vol. 47, pp. 8867–8871.

    Article  CAS  Google Scholar 

  239. Bouillon, C., Meyer, A., Vidal, S., Jochum, A., Chevolot, Y., Cloarec, J.-P., Praly, J.-P., Vasseur, J.J., and Morvan, F., J. Org. Chem., 2006, vol. 71, pp. 4700–4702.

    Article  CAS  PubMed  Google Scholar 

  240. Chevolot, Y., Bouillon, C., Vidal, S., Morvan, F., Meyer, A., Cloarec, J.-P., Jochum, A., Praly, J.-P., Vasseur, J.-J., and Souteyrand, E., Angew. Chem., Int. Ed. Engl., 2007, vol. 46, pp. 2398–2402.

    Article  CAS  Google Scholar 

  241. Devaraj, N.K., Miller, G.P., Ebina, W., Kakaradov, B., Collman, J.P., Kool, E.T., and Chidsey, C.E.D., J. Am. Chem. Soc., 2005, vol. 127, pp. 8600–8601.

    Article  CAS  PubMed  Google Scholar 

  242. Filichev, V.V. and Pedersen, E.B., J. Am. Chem. Soc., 2005, vol. 127, pp. 14849–14858.

    Article  CAS  PubMed  Google Scholar 

  243. Hong, V., Presolski, S.I., Ma, C., and Finn, M.G., Angew. Chem., Int. Ed. Engl., 2009, vol. 48, pp. 9879–9883.

    Article  CAS  Google Scholar 

  244. Ju, J., Kim, D.H., Bi, L., Meng, Q., Bai, X., Li, Z., Li, X., Marma, M.S., Shi, S., Wu, J., Edwards, J.R., Romu, A., and Turro, N.J., Proc. Natl. Acad. Sci. USA, 2006, vol. 103, pp. 19635–19640.

    Article  CAS  PubMed  Google Scholar 

  245. Perman, J., Sharma, R.A., and Bobek, M., Tetrahedron Lett., 1976, pp. 2427–2430.

  246. Korshun, V.A., Manasova, E.V., and Berlin, Yu.A., Bioorg. Khim., 1997, vol. 23, pp. 324–387 [Russ. J. Bioorg. Chem. (Eng. Transl.), 1997, vol. 23, pp. 300–362].

    CAS  Google Scholar 

  247. Biala, E., Jones, A.S., and Walker, R.T., Tetrahedron, 1980, vol. 36, pp. 155–158.

    Article  CAS  Google Scholar 

  248. Ötvös, L., Szécsi, J., Sági, J., and Kovácz, T., Nucleic Acids Symp. Ser., 1987, vol. 18, pp. 125–129.

    PubMed  Google Scholar 

  249. Kovacz, T. and Otvos, L., Tetrahedron Lett., 1988, vol. 29, pp. 4525–4528.

    Article  Google Scholar 

  250. Dolbeare, F., Histochem. J., 1995, vol. 27, pp. 339–369.

    CAS  PubMed  Google Scholar 

  251. Dolbeare, F., Histochem. J., 1996, vol. 28, pp. 531–575.

    Article  CAS  PubMed  Google Scholar 

  252. Taupin, P., Brain Res. Rev., 2007, vol. 53, pp. 198–214.

    Article  CAS  PubMed  Google Scholar 

  253. Dolbeare, F., Histochem. J., 1995, vol. 27, pp. 923–964.

    CAS  PubMed  Google Scholar 

  254. Salic, A. and Mitchison, T.J., Proc. Natl. Acad. Sci. USA, 2008, vol. 105, pp. 2415–2420.

    Article  CAS  PubMed  Google Scholar 

  255. Buck, S.B., Bradford, J., Gee, K.R., Agnew, B.J., Clarke, S.T., and Salic, A., BioTechniques, 2008, vol. 44, pp. 927–929.

    Article  CAS  PubMed  Google Scholar 

  256. Cappella, P., Gasparri, F., Pulici, M., and Moll, J., Current Prot. Cytometry, 2008, pp. 7.34.1–7.34.13.

  257. Cappella, P., Gasparri, F., Pulici, M., and Moll, J., Cytometry, 2008, vol. 73A, pp. 626–636.

    Article  CAS  Google Scholar 

  258. Burley, G.A., Gierlich, J., Mofid, M.R., Nir, H., Tal, S., Eichen, Y., and Carell, T., J. Am. Chem. Soc., 2006, vol. 128, pp. 1398–1399.

    Article  CAS  PubMed  Google Scholar 

  259. Chehrehasa, F., Meedeniya, A.C.B., Dwyer, P., Abrahamsen, G., and Mackay-Sim, A., J. Neurosci. Meth., 2009, vol. 177, pp. 122–130.

    Article  CAS  Google Scholar 

  260. Klein, R.M. and Aplin, A.E., Cancer Res., 2009, vol. 69, pp. 2224–2233.

    Article  CAS  PubMed  Google Scholar 

  261. Scheef, E.A., Sorenson, C.M., and Sheibani, N., Am. J. Physiol. Cell Physiol., 2008, vol. 296, pp. C724–C734.

    Article  CAS  Google Scholar 

  262. Szafran, A.T., Szwarc, M., Marcelli, M., and Mancini, M.A., PLoS One, 2008, vol. 3, p. e3605.

    Article  PubMed  CAS  Google Scholar 

  263. Bonaguidi, M.A., Peng, C.-Y., McGuire, T., Falciglia, G., Gobeske, K.T., Czeisler, C., and Kessler, J.A., J. Neurosci., 2008, vol. 28, pp. 9194–9204.

    Article  CAS  PubMed  Google Scholar 

  264. Hitomi, M., Yang, K., Stacey, A.W., and Stacey, D.W., Mol. Cell. Biol., 2008, vol. 28, pp. 5478–5493.

    Article  CAS  PubMed  Google Scholar 

  265. Jensen, U.B., Yan, X., Triel, C., Woo, S.-H., Christensen, R., and Owens, D.M., J. Cell Sci., 2008, vol. 121, pp. 609–617.

    Article  CAS  PubMed  Google Scholar 

  266. Huang, Q. and Sheibani, N., Am. J. Physiol. Cell Physiol., 2008, vol. 295, pp. C1647–C1657.

    Article  CAS  PubMed  Google Scholar 

  267. Walters, K.-A., Syder, A.J., Lederer, S.L., Diamond, D.L., Paeper, B., Rice, C.M., and Katze, M.G., PLoS One, 2009, vol. 5, p. e1000269.

    Google Scholar 

  268. Oberst, M.D., Beberman, S.J., Zhao, L., Yin, J.J., Ward, Y., and Kelly, K., BMC Cancer, 2008, vol. 8, p. 189.

    Article  PubMed  CAS  Google Scholar 

  269. Diermeier-Daucher, S., Clarke, S.T., Hill, D., Vollmann-Zwerenz, A., Bradford, J.A., and Brockhoff, G., Cytometry, 2009, vol. 75A, pp. 535–546.

    Article  CAS  Google Scholar 

  270. Hamelik, R.M. and Krishan, A., Cytometry, 2009, vol. 75A, pp. 862–865.

    Article  CAS  Google Scholar 

  271. Yu, Y., Arora, A., Min, W., Roifman, C.M., and Grunebaum, E., J. Immunol. Methods, 2009, vol. 350, pp. 29–35.

    Article  CAS  PubMed  Google Scholar 

  272. Kaiser, C.L., Kamien, A.J., Shah, P.A., Chapman, B.J., and Cotanche, D.A., The Laryngoscope, 2009, vol. 119, pp. 1770–1775.

    Article  PubMed  Google Scholar 

  273. Ferullo, D.J., Cooper, D.L., Moore, H.R., and Lovett, S.T., Methods, 2009, vol. 489, pp. 8–13.

    Article  CAS  Google Scholar 

  274. Aparicio, T., Guillou, E., Coloma, J., Montoyaand, G., and Méndez, J., Nucleic Acid Res., 2009, vol. 37, pp. 2087–2095.

    Article  CAS  PubMed  Google Scholar 

  275. Vidal-Cardenas, S.L. and Greider, C.W., Nucleic Acid Res., 2010, vol. 38, pp. 60–71.

    Article  CAS  PubMed  Google Scholar 

  276. Warren, M., Puskarczyk, K., and Chapman, S.C., Dev. Dynam., 2009, vol. 238, pp. 944–949.

    Article  CAS  Google Scholar 

  277. Limsirichaikul, S., Niimi, A., Fawcett, H., Lehmann, A., Yamashita, S., and Ogi, T., Nucleic Acid Res., 2009, vol. 37, e31.

    Article  PubMed  CAS  Google Scholar 

  278. Jao, C.Y. and Salic, A., Proc. Natl. Acad. Sci. USA, 2008, vol. 105, pp. 15779–15784.

    Article  CAS  PubMed  Google Scholar 

  279. Gramlich, P.M.E., Wirges, C.T., Gierlich, J., and Carell, T., Org. Lett., 2008, vol. 10, pp. 249–251.

    Article  CAS  PubMed  Google Scholar 

  280. Macicková-Cahová, H. and Hocek, M., Nucleic Acid Res., 2009, vol. 37, pp. 7612–7622.

    Article  PubMed  CAS  Google Scholar 

  281. Fischler, M., Sologubenko, A., Mayer, J., Clever, G., Burley, G., Gierlich, J., Carell, T., and Simon, U., Chem. Commun., 2008, pp. 169–171.

  282. Wirges, C.T., Gramlich, P.M.E., Gutsmiedl, K., Gierlich, J., Burley, G.A., and Carell, T., QSAR Comb. Sci., 2007, vol. 26, pp. 1159–1164.

    Article  CAS  Google Scholar 

  283. Fischler, M., Simon, U., Nir, H., Eichen, Y., Burley, G.A., Gierlich, J., Gramlich, P.M.E., and Carell, T., Small, 2007, vol. 3, pp. 1049–1055.

    Article  CAS  PubMed  Google Scholar 

  284. Lin, N., Yan, J., Huang, Z., Altier, C., Li, M., Carrasco, N., Suyemoto, M., Johnston, L., Wang, S., Wang, Q., Fang, H., Caton-Williams, J., and Wang, B., Nucleic Acid Res., 2007, vol. 35, pp. 1222–1229.

    Article  CAS  PubMed  Google Scholar 

  285. Weller, R.L. and Rajski, S.R., Org. Lett., 2005, vol. 7, pp. 2141–2144.

    Article  CAS  PubMed  Google Scholar 

  286. Punna, S., Kuzelka, J., Wang, Q., and Finn, M.G., Angew. Chem., Int. Ed. Engl., 2005, vol. 44, pp. 2215–2220.

    Article  CAS  Google Scholar 

  287. Burrows, C.J. and Muller, J.G., Chem. Rev., 1998, vol. 98, pp. 1109–1151.

    Article  CAS  PubMed  Google Scholar 

  288. Zatsepin, T.S. and Oretskaya, T.S., Chem. Biodivers., 2004, pp. 1401–1417.

  289. von Matt, P., Lochmann, T., and Altmann, K.-H., Bioorg. Med. Chem. Lett., 1997, vol. 7, pp. 1549–1552.

    Article  Google Scholar 

  290. Lazrek, H.B., Engels, J.W., and Pfleiderer, W., Nucleosides Nucleotides, 1998, vol. 17, pp. 1851–1856.

    Article  CAS  Google Scholar 

  291. O’Mahony, G., Ehrman, E., and Grötli, M., Tetrahedron Lett., 2005, vol. 46, pp. 6745–6748.

    Article  CAS  Google Scholar 

  292. Jin, P.-Y., Jin, P., Ruan, Y.-A., Ju, Y., and Zhao, Y.-F., Synlett., 2007, pp. 3003–3006.

  293. Malkoch, M., Schleicher, K., Drockenmuller, E., Hawker, C.J., Russell, T.P., Wu, P., and Fokin, V.V., Macromolecules, 2007, vol. 38, pp. 3663–3678.

    Article  CAS  Google Scholar 

  294. Plietzsch, O., Schilling, C.I., Tolev, M., Nieger, M., Richert, C., Muller, T., and Bräse, S., Org. Biomol. Chem., 2009, vol. 7, pp. 4734–4743.

    Article  CAS  PubMed  Google Scholar 

  295. Nuzzi, A., Massi, A., and Dondoni, A., QSAR Comb. Sci, 2007, vol. 26, pp. 1191–1199.

    Article  CAS  Google Scholar 

  296. Fujino, T., Marine, G., Nakamura, E., and Isobe, H., Nucleic Acids Symp. Ser., 2007, vol. 51, pp. 267–268.

    Article  CAS  Google Scholar 

  297. Isobe, H., Fujino, T., Yamazaki, N., Guillot-Nieckowski, M., and Nakamura, E., Org. Lett., 2008, vol. 10, pp. 3729–3732.

    Article  CAS  PubMed  Google Scholar 

  298. Fujino, T., Yamazaki, N., and Isobe, H., Tetrahedron Lett., 2009, vol. 50, pp. 4101–4103.

    Article  CAS  Google Scholar 

  299. Lucas, R., Neto, V., Bouazza, A.H., Zerrouki, R., Granet, R., Krausz, P., and Champavier, Y., Tetrahedron Lett., 2008, vol. 49, pp. 1004–1007.

    Article  CAS  Google Scholar 

  300. Lucas, R., Zerrouki, R., Granet, R., Krausz, P., and Champavier, Y., Tetrahedron, 2008, vol. 64, pp. 5467–5471.

    Article  CAS  Google Scholar 

  301. Blomquist, A.T. and Liu, L.H., J. Am. Chem. Soc., 1953, vol. 75, pp. 2153–2154.

    Article  CAS  Google Scholar 

  302. Wittig, G. and Krebs, A., Chem. Ber., 1961, vol. 94, pp. 3260–3275.

    Article  CAS  Google Scholar 

  303. Agard, N.J., Prescher, J.A., and Bertozzi, C.R., J. Am. Chem. Soc., 2004, vol. 126, pp. 15046–15047.

    Article  CAS  PubMed  Google Scholar 

  304. Agard, N.J., Baskin, J.M., Prescher, J.A., Lo, A., and Bertozzi, C.R., ACS Chem. Biol, 2006, vol. 1, pp. 644–648.

    Article  CAS  PubMed  Google Scholar 

  305. Baskin, J.M., Prescher, J.A., Laughlin, S.T., Agard, N.J., Chang, P.V., Miller, I.A., Lo, A., Codelli, J.A., and Bertozzi, C.R., Proc. Natl. Acad. Sci. USA, 2007, vol. 104, pp. 16793–16797.

    Article  CAS  PubMed  Google Scholar 

  306. Codelli, J.A., Baskin, J.M., Agard, N.J., and Bertozzi, C.R., J. Am. Chem. Soc., 2008, vol. 130, pp. 11486–11493.

    Article  CAS  PubMed  Google Scholar 

  307. Neef, A.B. and Schultz, C., Angew. Chem., Int. Ed. Engl., 2009, vol. 48, pp. 1498–1500.

    Article  CAS  Google Scholar 

  308. Sletten, E.M. and Bertozzi, C.R., Org. Lett., 2008, vol. 10, pp. 3097–3099.

    Article  CAS  PubMed  Google Scholar 

  309. Ning, X., Guo, J., Wolfert, M.A., and Boons, G.-J., Angew. Chem., Int. Ed. Engl., 2008, vol. 47, pp. 2253–2255.

    Article  CAS  Google Scholar 

  310. Poloukhtine, A.A., Mbua, N.E., Wolfert, M.A., Boons, G.-J., and Popik, V.V., J. Am. Chem. Soc., 2009, vol. 131, pp. 15769–15776.

    Article  CAS  PubMed  Google Scholar 

  311. Fernández-Suárez, M., Baruah, H., Martínez-Hernández, L., Xie, K.T., Baskin, J.M., Bertozzi, C.R., and Ting, A.Y., Nature Biotechnol., 2007, vol. 25, pp. 1483–1487.

    Article  CAS  Google Scholar 

  312. Laughlin, S.T. and Bertozzi, C.R., Proc. Natl. Acad. Sci. USA, 2009, vol. 106, pp. 12–17.

    Article  CAS  PubMed  Google Scholar 

  313. Laughlin, S.T., Baskin, J.M., Amacher, S.L., and Bertozzi, C.R., Science, 2008, vol. 320, pp. 664–667.

    Article  CAS  PubMed  Google Scholar 

  314. Gartner, Z.J. and Bertozzi, C.R., Proc. Natl. Acad. Sci. USA, 2009, vol. 106, pp. 4606–4610.

    Article  CAS  PubMed  Google Scholar 

  315. Lin, G., Huang, Y.-C., Shindel, A.W., Banie, L., Wang, G., Lue, T.F., and Lin, C.-S., Cytotherapy, 2009, vol. 11, pp. 864–873.

    Article  PubMed  CAS  Google Scholar 

  316. Ande, S.R., Moulik, S., and Mishra, S., PLoS One, 2009, vol. 4, p. e4586.

    Article  PubMed  CAS  Google Scholar 

  317. Guo, J., Yu, L., Turro, N., and Ju, J., Acc. Chem. Res., 2010, vol. 43, pp. 551–563.

    Article  CAS  PubMed  Google Scholar 

  318. Karskela, M., Helkearo, M., Virta, P., and Lönnberg, H., Bioconjugate Chem., 2010, vol. 21, pp. 748–755.

    Article  CAS  Google Scholar 

  319. Yamaguchi, K., Sakai, M., Shimokawa, T., Yamada, Y., Nakamura, Y., and Furukawa, Y., Br. J. Cancer, 2010, vol. 102, pp. 325–331.

    Article  CAS  PubMed  Google Scholar 

  320. Beyer, C. and Wagenknecht, H.-A., Chem. Commun., 2010, vol. 46, pp. 2230–2231.

    Article  CAS  Google Scholar 

  321. Cutler, J.I., Zheng, D., Xu, X., Giljohann, D.A., and Mirkin, C.A., Nano Lett., 2010, vol. 10, pp. 1477–1480.

    Article  CAS  PubMed  Google Scholar 

  322. Voigt, N.V., Tørring, T., Rotaru, A., Jacobsen, M.F., Ravnsbæk, J.B., Subramani, R., Mamdouh, W., Kjems, J., Mokhir, A., Besenbacher, F., and Gothelf, K.V., Nature Nanotechnol., 2010, vol. 5, pp. 200–203.

    Article  CAS  Google Scholar 

  323. Jewett, J.C. and Bertozzi, C.R., Chem. Soc. Rev., 2010, vol. 39, pp. 1272–1279.

    Article  CAS  PubMed  Google Scholar 

  324. El-Sagheer, A.H. and Brown, T., Chem. Soc. Rev., 2010, vol. 39, pp. 1388–1405.

    Article  CAS  PubMed  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. Ustinov, I. A. Stepanova, V. V. Dubnyakova, E. V. Nozhevnikova & V. A. Korshun

  2. Moscow State University, Moscow, Russia

    T. S. Zatsepin

  3. Central Research Institute of Epidemiology, Moscow, Russia

    T. S. Zatsepin

Authors
  1. A. V. Ustinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. A. Stepanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Dubnyakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. S. Zatsepin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. V. Nozhevnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. A. Korshun
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Korshun.

Additional information

Original Russian Text © A.V. Ustinov, I.A. Stepanova, V.V. Dubnyakova, T.S. Zatsepin, E.V. Nozhevnikova, V.A. Korshun, 2010, published in Bioorganicheskaya Khimiya, 2010, Vol. 36, No. 4, pp. 437–481.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ustinov, A.V., Stepanova, I.A., Dubnyakova, V.V. et al. Modification of nucleic acids using [3 + 2]-dipolar cycloaddition of azides and alkynes. Russ J Bioorg Chem 36, 401–445 (2010). https://doi.org/10.1134/S1068162010040011

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162010040011

Key words

Search

Navigation