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Calixarenes as Supramolecular Catalysts Endowed with Esterase and Phosphodiesterase Activity

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Calixarenes and Beyond

Abstract

The molecular framework of calixarenes has been widely used as a versatile scaffold for the arrangement of active units working as catalytic and/or recognition sites, attaining, in many cases, high levels of cooperation. The calixarene cavity itself can also play a role in the catalytic process, acting as a recognition unit by inclusion of the substrate or of part of the substrate. This chapter focuses on the high performance of calixarene catalysts active in acyl and phosphoryl transfer processes.

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References

  1. (a) Breslow, R., Ed. Artificial Enzymes; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005; (b) van Leeuwen, P. W. N. M., Ed. Supramolecular Catalysis; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2008; (c) Brinker, U. H., Mieusset, J.-L., Eds. Molecular Encapsulation – Organic Reactions in Constrained Systems; John Wiley & Sons, Ltd.: New York, 2010. (d) Raynal, M.; Ballester, P.; Vidal – Ferran, A.; Van Leeuwen, P. W. N. M. Chem. Soc. Rev. 2014, 43, 1734–1787.

    Google Scholar 

  2. Molenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75−86.

    Article  CAS  Google Scholar 

  3. (a) Weston, J. Chem. Rev. 2005, 105, 2151–2174; (b) Cowan, J. A. Chem. Rev. 1998, 98, 1067−1087; (c) Wilcox, D. E. Chem. Rev. 1996, 96, 2435−2458.

    Google Scholar 

  4. (a) Williams, N. H.; Takasaki, B.; Wall, M.; Chin, J. Acc. Chem. Res. 1999, 32, 485–493; (b) Mancin, F.; Scrimin, P.; Tecilla, P. Chem. Commun. 2012, 48, 5545−5559; and references therein.

    Google Scholar 

  5. (a) Gruber, B.; Kataev, E.; Aschenbrenner, J.; Stadlbauer, S.; König, B. J. Am. Chem. Soc. 2011, 133, 20704−20707; (b) Panja, A.; Matsuo, T.; Nagao, S.; Hirota, S. Inorg. Chem. 2011, 50, 11437−11445; (c) Linjalahti, H.; Feng, G. Q.; Mareque-Rivas, J. C.; Mikkola, S.; Williams, N. H. J. Am. Chem. Soc. 2008, 130, 4232−4233; (d) Nwe, K.; Andolina, C. M.; Morrow, J. R. J. Am. Chem. Soc. 2008, 130, 14861−14871; (e) Wang, Q.; Lönnberg, H. J. Am. Chem. Soc. 2006, 128, 10716−10728; (f) O’Donoghue, A.; Pyun, S. Y.; Yang, M. Y.; Morrow, J. R.; Richard, J. P. J. Am. Chem. Soc. 2006, 128, 1615−1621; (g) Neverov, A. A.; Lu, Z. -L.; Maxwell, C. I.; Mohamed, M. F.; White, C. J.; Tsang, J. S. W.; Brown, R. S. J. Am. Chem. Soc. 2006, 128, 16398−16405.

    Google Scholar 

  6. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Org. Chem. 2005, 70, 624−630.

    Article  CAS  Google Scholar 

  7. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Org. Chem. 2005, 70, 5398−5402.

    Article  CAS  Google Scholar 

  8. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. Inorg. Chim. Acta 2007, 360, 981−986.

    Article  CAS  Google Scholar 

  9. (a) Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Ungaro, R. J. Am. Chem Soc. 1992, 114, 10956−10958; (b) Baldini, L.; Bracchini, C.; Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Ungaro, R. Chem. Eur. J. 2000, 6, 1322−1330.

    Google Scholar 

  10. Cacciapaglia, R.; Mandolini, L. Chem. Soc. Rev. 1993, 22, 221−231.

    Article  CAS  Google Scholar 

  11. Kraft, D.; Böhmer, V.; Cacciapaglia, R.; Mandolini, L., Vogt, W. unpublished results.

    Google Scholar 

  12. Cacciapaglia, R.; Casnati, A.; Di Stefano, S.; Mandolini, L.; Paolemili, D.; Reinhoudt, D. N.; Sartori, A.; Ungaro, R. Chem Eur. J. 2004, 10, 4436−4442.

    Article  CAS  Google Scholar 

  13. (a) Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183−278; (b) Mandolini, L. Adv. Phys. Org. Chem. 1986, 22, 1−111.

    Google Scholar 

  14. (a) Cacciapaglia, R.; Di Stefano, S.; Mandolini, L. Acc. Chem. Res. 2004, 37, 113−122; (b) Di Stefano, S.; Cacciapaglia, R.; Mandolini, L. Eur. J. Org. Chem. 2014, 7304−7315.

    Google Scholar 

  15. Cacciapaglia, R.; Di Stefano, S.; Kelderman, E.; Mandolini, L. Angew. Chem. Int. Ed. 1999, 38, 348−351.

    Article  CAS  Google Scholar 

  16. Molenveld, P.; Kapsabelis, S.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1997, 119, 2948−2949.

    Article  CAS  Google Scholar 

  17. Molenveld, P.; Stikvoort, W. M. G.; Kooijman, H.; Spek, A. L.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1999, 64, 3896−3906.

    Article  CAS  Google Scholar 

  18. Molenveld, P.; Engbersen, J. F. J.; Kooijman, H.; Spek, A. L.; Reinhoudt, D. N. J. Am. Chem. Soc. 1998, 120, 6726−6737.

    Article  CAS  Google Scholar 

  19. Sträter, N.; Lipscomb, W. N.; Klabunde, T.; Krebs, B. Angew. Chem. Int. Ed. 1996, 35, 2024−2055.

    Article  Google Scholar 

  20. Molenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem. Int. Ed. 1999, 38, 3189−3192.

    Article  CAS  Google Scholar 

  21. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Am. Chem. Soc. 2006, 128, 12322–12330.

    Article  CAS  Google Scholar 

  22. Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Peracchi, A.; Reinhoudt, D. N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Am. Chem. Soc. 2007, 129, 12512−12520.

    Article  CAS  Google Scholar 

  23. Cotton, F. A.; Hazen, E. E., Jr.; Legg, M. J. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2551−2555.

    Google Scholar 

  24. For a recent review article see: Salvio, R. Chem. Eur. J. 2015, 21, 10960−10971.

    Google Scholar 

  25. (a) Suh, J.; Moon, S. -J. Inorg. Chem. 2001, 40, 4890−4895; (b) Ait-Haddou, H.; Sumaoka, J.; Wiskur, S. L.; Folmer-Andersen, J. F.; Anslyn, E. V. Angew. Chem., Int. Ed. 2002, 41, 4014−4016; (c) Piatek, A. M.; Gray, M.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 9878−9879; (d) Scheffer, U.; Strick, A.; Ludwig, V.; Peter, S.; Kalden, E.; Göbel, M. W. J. Am. Chem. Soc. 2005, 127, 2211−2217; (e) Gnaccarini, C.; Peter, S.; Scheffer, U.; Vonhoff, S.; Klussmann, S.; Göbel, M. W. J. Am. Chem. Soc. 2006, 128, 8063−8067; (f) Lindgren, N. J. V.; Lars Geiger, J.R.; Schmuck, C.; Baltzer, L. Angew. Chem., Int. Ed. 2009, 48, 6722−6725; (g) Corona-Martinez, D. O.; Taran, O.; Yatsimirsky, A. K. Org. Biomol. Chem. 2010, 8, 873−880; (h) Salvio, R.; Cacciapaglia, R.; Mandolini, L. J. Org. Chem. 2011, 76, 5438–5443; (i) Salvio, R.; Mandolini, L.; Savelli, C. J. Org. Chem. 2013, 78, 7259−7263; (j) Savelli, C.; Salvio, R. Chem. Eur. J. 2015, 21, 5856−5863; (k) Salvio, R.; Cincotti, A. RSC Adv. 2014, 4, 28678−28682.

    Google Scholar 

  26. Baldini, L.; Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Salvio, R.; Sansone, F.; Ungaro, R. J. Org. Chem. 2012, 77, 3381−3389.

    Article  CAS  Google Scholar 

  27. Salvio, R.; Cacciapaglia, R.; Mandolini, L.; Sansone, F.; Casnati, A. RSC Adv. 2014, 4, 34412−34416.

    Article  CAS  Google Scholar 

  28. Salvio, R.; Casnati, A.; Mandolini, L.; Sansone, F.; Ungaro, R. Org. Biomol. Chem. 2012, 10, 8941−8943.

    Article  CAS  Google Scholar 

  29. (a) Hosseini, M. W.; Lehn, J. -M.; Jones, K. C.; Plute, K. E.; Mertes, K. B.; Mertes, M. P. J. Am. Chem. Soc. 1989, 111, 6330−6335; (b) Hosseini, M. W.; Lehn, J. -M.; Maggiora, L.; Mertes, K. B.; Mertes, M. P. J. Am. Chem. Soc. 1987, 109, 537−544; (c) Hosseini, M. W.; Lehn, J. -M.; Mertes, M. P. Helv. Chim. Acta 1983, 66, 2454−2466.

    Google Scholar 

  30. Salvio, R.; Volpi, S.; Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Sansone, F. J. Org. Chem. 2015, 80, 5887−5893.

    Article  CAS  Google Scholar 

  31. For the desymmetryzation of calix[4]arenes, see also: (a) Ciaccia, M.; Tosi, I.; Cacciapaglia, R.; Casnati, A.; Baldini, L.; Di Stefano, S. Org. Biomol. Chem. 2013, 11, 3642–3648. (b) Galli, M.; Berrocal, J. A.; Di Stefano, S.; R. Cacciapaglia; L. Mandolini; L. Baldini; A. Casnati; F. Ugozzoli Org. Biomol. Chem. 2012, 10, 5109−5112.

    Google Scholar 

  32. Hioki, H.; Nishimoto, R, Kawaguchi, K.; Kubo, M.; Harada, K.; Fukuyama, Y. Chem. Commun. 2009, 7194−7196.

    Google Scholar 

  33. Yang, H.; Sherman, J. C. Bioorg. Med. Chem. Lett. 2013, 23, 1752−1753

    Article  CAS  Google Scholar 

  34. Shinkai, S.; Mori, S.; Koreishi, H.; Tsubaki T.; Manabe, O. J. Am. Chem. Soc. 1986, 108, 2409−2416.

    Article  CAS  Google Scholar 

  35. Goto, K.; Yano, Y.; Okada, E.; Liu, C. -W.; Yamamoto, K.; Ueoka, R. J. Org. Chem. 2003, 68, 865−870.

    Google Scholar 

  36. Almeida, C. G.; Souza, I. F.; Liberto, N. A.; Da Silva, M. J.; Fernandes S. A.; Le Hyaric M. Monatsh. Chem. 2015, 146, 1927−1934.

    Article  CAS  Google Scholar 

  37. (a) Magrans, J.O.; Ortiz, A.R.; Molins, A.; Lebouille, P.H.P.; Sánchez-Quesada, J.; Prados, P.; Pons, M.; de Mendoza, J. Angew. Chem. Int. Ed. 1996 , 35, 1712−1715; (b) Cuevas, F.; Di Stefano, S.; Magrans, J. O.; Prados, P.; Mandolini, L.; de Mendoza, J. Chem. Eur. J. 2000, 6, 3228−3234.

    Google Scholar 

  38. See for example: (a) Arduini, A.; Brindani, E.; Giorgi, G.; Pochini, A.; Secchi, A. J. Org. Chem. 2002, 67, 6188−6194; (b) Arduini, A.; Brindani, E.; Giorgi, G.; Pochini, A.; Secchi, A. Tetrahedron 2003, 59, 75877594; and references therein.

    Google Scholar 

  39. (a) Richeter, S.; Rebek, J., Jr. J. Am. Chem. Soc. 2004, 126, 16280−16281; (b) Zelder, F. H.; Salvio, R.; Rebek, J., Jr. Chem. Commun. 2006, 1280−1282.

    Google Scholar 

  40. Gissot, A.; Rebek, J., Jr. J. Am. Chem. Soc. 2004, 126, 7424−7425.

    Article  CAS  Google Scholar 

  41. Soberats, B.; Sanna, E.; Martorell, G.; Rotger, C.; Costa, A. Org Lett. 2013, 16, 840−843.

    Article  Google Scholar 

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Correspondence to Alessandro Casnati .

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Salvio, R., Cacciapaglia, R., Casnati, A. (2016). Calixarenes as Supramolecular Catalysts Endowed with Esterase and Phosphodiesterase Activity. In: Neri, P., Sessler, J., Wang, MX. (eds) Calixarenes and Beyond. Springer, Cham. https://doi.org/10.1007/978-3-319-31867-7_26

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