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Achievements in the synthesis of cyclooctynes for ring strain-promoted [3+2] azide-alkyne cycloaddition

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Chemistry of Heterocyclic Compounds Aims and scope

The aim of this review is to present the entire range of cyclooctynes that are currently known in the literature. We provide a generalized and systematic overview of methods for their synthesis and consider the applications of cyclooctynes for the purposes of molecular biology and cellular engineering. The importance of cyclooctynes for [3+2] azide-alkyne cycloaddition is demonstrated, as the high reactivity of cyclooctynes allows to perform this reaction under mild conditions without a catalyst.

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References

  1. Michael, A. J. Prakt. Chem. 1893, 48, 94.

    Article  Google Scholar 

  2. Huisgen, R. Angew. Chem., Int. Ed. 1963, 2, 565.

    Article  Google Scholar 

  3. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.

    Article  CAS  Google Scholar 

  4. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.

    Article  CAS  PubMed  Google Scholar 

  5. Singh, M. S.; Chowdhury, S.; Koley, S. Tetrahedron 2016, 72, 5257.

    Article  CAS  Google Scholar 

  6. a Horisawa, K. Front. Physiol. 2014, 5, 1. b Ishizuka, T.; Liu, H. S.; Ito, K.; Xu, Y. Sci. Rep. 2016, 6, 1.

  7. а Jao, C. Y.; Salic, A. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 15779. b Salic, A.; Mitchison, T. J. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 2415.

  8. Saxon, E.; Bertozzi, C. R. Science 2000, 287, 2007.

    Article  CAS  PubMed  Google Scholar 

  9. Wittig, G.; Krebs, A. Chem. Ber. 1961, 94, 3260.

    Article  CAS  Google Scholar 

  10. Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2004, 126, 15046.

    Article  CAS  PubMed  Google Scholar 

  11. Chang, P. V.; Bertozzi, C. R. Chem. Commun. 2012, 48, 8864.

    Article  CAS  Google Scholar 

  12. Möller, H.; Böhrsch, V.; Bentrop, J.; Bender, J.; Hinderlich, S.; Hackenberger, C. Angew. Chem., Int. Ed. 2012, 51, 5986.

    Article  CAS  Google Scholar 

  13. Jewett, J. C.; Bertozzi, C. R. Org. Lett. 2011, 13, 5937.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Horner, K. A.; Valette, N. M.; Webb, M. E. Chem.–Eur. J. 2015, 21, 14376.

    Article  CAS  PubMed  Google Scholar 

  15. Wang, D.; Viennois, E.; Ji, K.; Damera, K.; Draganov, A.; Zheng, Y.; Dai, C.; Merlin, D.; Wang, B. Chem. Commun. 2014, 50, 15890.

    Article  CAS  Google Scholar 

  16. Agarwal, P.; Beahm, B. J.; Shieh, P.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2015, 54, 11504.

    Article  CAS  Google Scholar 

  17. Singh, I.; Heaney, F. Chem. Commun. 2011, 47, 2706.

    Article  CAS  Google Scholar 

  18. Qian, L.; Zhang, C.-J.; Wu, J.; Yao, S. Q. Chem.–Eur. J. 2017, 23, 360.

    Article  CAS  PubMed  Google Scholar 

  19. (a) Kirmse, W.; Horner, L. Liebigs Ann. Chem. 1958, 1, 614. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057. (c) Kiick, K. L.; Saxon, E.; Tirrel, D. A.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 19. (d) Debets, M. F.; van Berkel, S. S.; Dommerholt, J. A. N.; Dirks, T. J.; Rutjes, F. P. J. T.; van Delft, F. L. Acc. Chem. Res. 2011, 44, 805.

  20. Meier, H.; Petersen, H.; Kolshorn, H. Chem. Ber. 1980, 113, 2398.

    Article  CAS  Google Scholar 

  21. Turner, R.; Jarrett, A. D.; Goebel, P.; Mallon, B. J. J. Am. Chem. Soc. 1973, 95, 790.

    Article  CAS  Google Scholar 

  22. Shea, K. J.; Kim, J. S. J. Am. Chem. Soc. 1992, 114, 4846.

    Article  CAS  Google Scholar 

  23. Sanders, B. C.; Friscourt, F.; Ledin, P. A.; Mbua, N. E.; Arumugam, S.; Guo, J.; Boltje, T. J.; Popik, V. V.; Boons, G.-J. J. Am. Chem. Soc. 2011, 133, 949.

    Article  CAS  PubMed  Google Scholar 

  24. Sauer, J.; Heldmann, D. K.; Hetzenegger, J.; Krauthan, J.; Sichert, H.; Schuster, J. Eur. J. Org. Chem. 1998, 12, 2885.

    Article  Google Scholar 

  25. Chen, W.; Wang, D.; Dai, C.; Hamelberg, D.; Wang, B. Chem. Commun. 2012, 48, 1736.

    Article  CAS  Google Scholar 

  26. Borrmann, A.; Milles, S.; Plass, T.; Dommerholt, J.; Verkade, J. M. M.; Wießler, M.; Schultz, C.; van Hest, J. C. M.; van Delft, F. L.; Lemke, E. A. ChemBioChem 2012, 13, 2094.

    Article  CAS  PubMed  Google Scholar 

  27. Sletten, E. M.; Bertozzi, C. R. Acc. Chem. Res. 2011, 44, 666.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Reese, B.; Shaw, A. J. Chem. Soc. D 1970, 1172.

  29. Bistrup, A.; Bhakta, S.; Lee, J. K.; Belov, Y. Y.; Gunn, M. D.; Zuo, F.-R.; Huang, C.-C.; Kannagi, R.; Rosen, S. D.; Hemmerich, S. J. Cell Biol. 1999, 145, 899.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Luchansky, S. J.; Argade, S.; Hayes, B. K.; Bertozzi, C. R. Biochemistry 2004, 43, 12358.

    Article  CAS  PubMed  Google Scholar 

  31. Hagendorrn, T.; Bräse, S. Eur. J. Org. Chem. 2014, 6, 1280.

    Article  CAS  Google Scholar 

  32. Banert, K.; Plefka, O. Angew. Chem., Int. Ed. 2011, 50, 6171.

    Article  CAS  Google Scholar 

  33. Agard, N. J.; Baskin, J. M.; Prescher, J. A.; Lo A.; Bertozzi, C. R. ACS Chem. Biol. 2006, 1, 644.

    Article  CAS  PubMed  Google Scholar 

  34. Jewett, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. Kostova, V.; Dransart, E.; Azoulay, M.; Brulle, L.; Bai, S.-K.; Florent, J.-C.; Johannes, L.; Schmidt, F. Bioorg. Med. Chem. 2015, 23, 7150.

    Article  CAS  PubMed  Google Scholar 

  36. Sletten, E. M.; Nakamura, H.; Jewett, J. C.; Bertozzi, C. R. J. Am. Chem. Soc. 2010, 132, 11799.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Codelli, J. A.; Baskin, J. M.; Agard, N. J.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 11486.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. Pirrung, M. C.; Webster, N. J. G. J. Org. Chem. 1987, 52, 3603.

    Article  CAS  Google Scholar 

  39. Banks, R. E.; Lawrence, N. J.; Popplewell, A. L. Chem. Commun. 1994, 343.

  40. Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 16793.

    Article  PubMed  PubMed Central  Google Scholar 

  41. Ning, X.; Guo, J.; Wolfert, M. A.; Boons, G. Angew. Chem., Int. Ed. 2008, 47, 2253.

    Article  CAS  Google Scholar 

  42. Jung, M. E.; Miller, S. J. J. Am. Chem. Soc. 1981, 103, 1984.

    Article  CAS  Google Scholar 

  43. Mbua, N. E.; Guo, J.; Wolfert, M. A.; Steet, R.; Boons, G.-J. ChemBioChem 2011, 12, 1912.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  44. Friscourt, F.; Fahrni, C. J.; Boons, G.-J. J. Am. Chem. Soc. 2012, 134, 18809.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  45. Dommerholt, J.; Schmidt, S.; Temming, R.; Hendriks, L. J. A.; Rutjes, F. P. J. T.; van Hest, J. C. M.; Lefeber, D. J.; van Delft, F. L. Angew. Chem., Int. Ed. 2010, 49, 9422.

    Article  CAS  Google Scholar 

  46. Munster, N.; Nikodemiak, P.; Koert, U. Org. Lett. 2016, 18, 4296.

    Article  CAS  PubMed  Google Scholar 

  47. Gordon, C. G.; Macкey, J. L.; Jewett, J. C.; Sletten, E. M.; Houk, K. N.; Bertozzi, C. R. J. Am. Chem. Soc. 2012, 134, 9199.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. Jewett, J. C.; Sletten, E. M.; Bertozzi, C. R. J. Am. Chem. Soc. 2010, 132, 3688.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  49. Brown, D. W.; Graupner, P. R.; Sainsbury, M.; Shertzer, H. G. Tetrahedron 1991, 47, 4383.

    Article  CAS  Google Scholar 

  50. Debets, M. F.; van Berkel, S. S.; Schoffelen, S.; Rutjes, F. P. J. T.; van Hest, J. C. M.; van Delft, F. L. Chem. Commun. 2010, 46, 97.

  51. Sletten, E. M.; Bertozzi, C. R. Org. Lett. 2008, 10, 3097.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  52. Jones, K.; Wood, W. W. Carbohydr. Res. 1986, 155, 217.

    Article  CAS  Google Scholar 

  53. de Almeida, G.; Sletten, E. M.; Nakamura, H.; Palaniappan, K. K.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2012, 51, 2443.

    Article  CAS  Google Scholar 

  54. Mcnitt, C. D.; Popik, V. V. Org. Biomol. Chem. 2012, 10, 8200.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. van Delft, P.; de Witte, W.; Meeuwenoord, N. J.; van Der Heden van Noort, G. J.; Versluis, F.; Olsthoorn, R. C. L.; Overkleeft, H. S.; van der Marel, G. A.; Filippov, D. V. Eur. J. Org. Chem. 2014, 34, 7566.

  56. Gröst, C.; Berg, T. Org. Biomol. Chem. 2015, 13, 3866.

    Article  PubMed  Google Scholar 

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This study received financial support from the Russian Foundation for Basic Research (grant 17-33-50091).

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Authors and Affiliations

  1. Institute of Living Systems, Immanuel Kant Baltic Federal University, 2a Universitetskaya St, Kaliningrad, 236016, Russia

    Evgeny G. Chupakhin & Mikhail Yu. Krasavin

  2. Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Petergof, Saint Petersburg, 198504, Russia

    Mikhail Yu. Krasavin

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  1. Evgeny G. Chupakhin
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Correspondence to Mikhail Yu. Krasavin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(5), 483–501

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Chupakhin, E.G., Krasavin, M.Y. Achievements in the synthesis of cyclooctynes for ring strain-promoted [3+2] azide-alkyne cycloaddition. Chem Heterocycl Comp 54, 483–501 (2018). https://doi.org/10.1007/s10593-018-2295-x

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