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Calixarenes in Organo and Biomimetic Catalysis

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Book cover Calixarenes and Beyond

Abstract

Organocatalysis and biocatalysis have emerged as new and powerful tools especially in asymmetric synthesis. This survey is focused to have an overview of calixarene based organo- and biomimetic catalysis. Calix[n]arenes constitute a fascinating class of macrocycles that have found a broad spectrum of applications in supramolecular chemistry and molecular recognition. The scope of the present review is to provide an overview of applications of calixarene-based materials in asymmetric catalysis and biomimetic catalysis.

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References

  1. Da Silva, D.L.; Fernandes, S.A.; Sabino, A.A.; de Fatima, A. Tetrahedron Lett. 2011, 52, 6328–6330.

    Article  Google Scholar 

  2. Dalko, P.I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138–5175.

    Article  CAS  Google Scholar 

  3. Berkessel, A.; Gröger, H. Chapter 8: Cycloaddition Reactions. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis. Weinheim: Wiley-VCH. 2005, p. 256–268. ISBN 3-527-30517-3.

    Google Scholar 

  4. Amarante, G.W.; Coelho, F. Quim. Nova 2009, 32, 469–481.

    Article  CAS  Google Scholar 

  5. Eymur, S.; Akceylan, E.; Sahin, O.; Uyanik, A.; Yilmaz, M. Tetrahedron 2014, 70, 4471–4477.

    Article  CAS  Google Scholar 

  6. Xu, Z.-X.; Li, G.-K.; Chen, C.-F.; Huang, Z.-T. Tetrahedron 2008, 64, 8668–8675.

    Article  CAS  Google Scholar 

  7. (a) Uyanik, A.; Bayrakci, M.; Eymur, S.; Yilmaz, M. Tetrahedron 2014, 70, 9307–9313.; (b) Durmaz, M.; Sirit, A. Tetrahedron: Asymmetry 2013, 24, 1443–1448.

    Google Scholar 

  8. Bocchi, V.; Foina, D.; Pochini, A.; Ungaro, R.; Andreetti, G.D. Tetrahedron 1982, 38, 373–378.

    Article  CAS  Google Scholar 

  9. Ungaro, R.; Pochini, A.; Andreetti, G.D.; Domiano, P. J. Inclusion Phenom. 1985, 3, 35–42.

    Article  CAS  Google Scholar 

  10. Ungaro, R.; Pochini, A.; Andreetti, G.D.; Ugozzoli, F. J. Inclusion Phenom. 1985, 3, 409–420.

    Article  CAS  Google Scholar 

  11. Nomura, E.; Taniguchi, H.; Kawaguchi, K.; Otsuji, Y. Chem. Lett. 1991, 20, 2167–2170.

    Article  Google Scholar 

  12. Nomura, E.; Taniguchi, H.; Kawaguchi, K.; Otsuji, Y. J. Org. Chem. 1993, 58, 4709–4715.

    Article  CAS  Google Scholar 

  13. Shimizu, S.; Shirakawa, S.; Sasaki, Y.; Hirai, C. Adv. Synth. Catal. 2002, 344, 370–378.

    Article  CAS  Google Scholar 

  14. Shimizu, S.; Shirakawa, S.; Suzuki, T.; Sasaki, Y. Tetrahedron 2001, 57, 6169–6173.

    Article  CAS  Google Scholar 

  15. Shirakawa, S.; Shimizu, S. Eur. J. Org. Chem. 2009, 1916–1924.

    Google Scholar 

  16. Yilmaz, M, Sayin, S. Chapter 2: Organic based magnetic nanoparticles-polymers and various calixarene based magnetic nanoparticles. Magnetic Nanoparticles: Properties, Synthesis and Applications. Nova Science Publishers, Inc. New York. 2012, p. 95–134. ISBN 978-1-61942-424-1.

    Google Scholar 

  17. Araki, K.; Yanagi, A.; Shinkai, S. Tetrahedron 1993, 49, 6763–6772.

    Article  CAS  Google Scholar 

  18. Shimizu, S.; Kito, K.; Sasaki, Y.; Hirai, C. Chem. Commun. 1997, 1629–1630.

    Google Scholar 

  19. Akceylan, E.; Yilmaz, M. Tetrahedron 2011, 67, 6240–6245.

    Article  CAS  Google Scholar 

  20. Srivastava, P.; Srivastava, R. Tetrahedron Lett. 2007, 48, 4489–4493

    Article  CAS  Google Scholar 

  21. Yang, F.; Guo, H.; Jiao, Z.; Li, C.; Ye, J. J. Iran Chem. Soc. 2012, 9, 327–332.

    Article  CAS  Google Scholar 

  22. Sayin, S.; Yilmaz, M. RSC Adv. 2014, 4, 2219–2225

    Article  CAS  Google Scholar 

  23. Shimizu, S.; Shimada, N.; Sasaki, Y. Green Chem. 2006, 608–614

    Google Scholar 

  24. Xie, Y.; Mao, L.; Li, L. J. Chem. Res. 2013, 476–479.

    Google Scholar 

  25. Sayin, S.; Yilmaz, M. Tetrahedron 2014, 70, 6669–6676

    Article  CAS  Google Scholar 

  26. Akceylan, E.; Uyanik, A.; Eymur, S.; Sahin, O; Yilmaz, M. Appl. Catal. A: Gen. 2015, 499, 205–212

    Article  CAS  Google Scholar 

  27. Sahin, O.; Erdemir, S.; Uyanik, A.; Yilmaz, M. Appl. Catal. A: Gen. 2009, 369, 36–41.

    Article  CAS  Google Scholar 

  28. Akceylan, E.; Akoz, E.; Sahin, O.; Yilmaz, M. J Incl Phenom Macrocycl Chem 2015, 81, 237–243.

    Article  CAS  Google Scholar 

  29. Akoz, E.; Akbulut, O.Y.; Yilmaz, M. Appl. Biochem. Biotechnol. 2014, 172, 509–523.

    Article  CAS  Google Scholar 

  30. Okahata, Y.; Ijiro, K. J. Chem. Soc., Chem. Commun. 1988, 1392–1394.

    Google Scholar 

  31. Goto, M.; Sumura, H.; Abe, K.; Nakashio, F. Biotechnol. Tech. 1995, 9, 101–104.

    CAS  Google Scholar 

  32. Pires, M.J.; Aires-Barros, M.R.; Cabral, J.M.S. Biotechnol. Prog. 1996, 12, 290–301.

    Article  CAS  Google Scholar 

  33. Inada, Y.; Takahashi, K.; Yoshimoto, T.; Ajima, A.; Matsushima, A.; Saito, Y. Trends Biotechnol. 1986, 4, 190–194.

    Article  CAS  Google Scholar 

  34. Oshima, T.; Sato, M.; Shikaze, Y.; Ohto, K.; Inoue, K.; Baba, Y. Biochem. Eng. J. 2007, 35, 66–70.

    Article  CAS  Google Scholar 

  35. 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 

  36. Hollenstein, M.; Hipolito, C.J.; Lam, C.H.; Perrin, D.M. ChemBioChem 2009, 10, 1988–1992.

    Article  CAS  Google Scholar 

  37. 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 

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

    Article  CAS  Google Scholar 

  39. Rebilly, J.-N.; Reinaud, O. Supramol. Chem. 2014, 26, 454–479.

    Article  CAS  Google Scholar 

  40. (a)Choi, K.H.; Shi, J.; Hopkins, C.E.; Tolan, D.R.; Allen, K.N. Biochemistry 2001, 40, 13868–13875. (b) Gutsche, C.D. Acc. Chem. Res. 1983, 16, 161–170.

    Google Scholar 

  41. Tabakci, B.; Yilmaz, M.; Beduk, A.D. J. Appl. Polym. Sci. 2012, 125, 1012–1019.

    Article  CAS  Google Scholar 

  42. Sayin, S.; Yilmaz, E.; Yilmaz, M. Org. Biomol. Chem. 2011, 9, 4021–4024.

    Article  CAS  Google Scholar 

  43. Jaeger, K.E; Eggert, T. Curr. Opin. Biotechnol. 2004, 15, 305–313.

    Article  CAS  Google Scholar 

  44. Ozyilmaz, E.; Sayin, S. Appl. Biochem. Biotechnol. 2013, 170, 1871–1884.

    Article  CAS  Google Scholar 

  45. Gotor-Fernández, V.; Brieva, R.; Gotor, V. J. Mol. Catal. B: Enzym. 2006, 40, 111–120.

    Article  Google Scholar 

  46. Koeller, K.M.; Wong, C.H. Nature 2001, 409, 232–240.

    Article  CAS  Google Scholar 

  47. Petsko, G.A.; Ringe, D. Chapter 1: From sequence to structure. Protein structure and function. London: New Science. 2003, p. 27. ISBN 978-1405119221.

    Google Scholar 

  48. Yilmaz, E.; Sezgin, M.; Yilmaz, M. Biocatal. Biotransform. 2009, 27, 360–366

    Article  CAS  Google Scholar 

  49. Yilmaz, E.; Can, K.; Sezgin, M.; Yilmaz, M. Bioresource Technol. 2011, 102, 499–506

    Article  CAS  Google Scholar 

  50. Tutar, H.; Yilmaz, E.; Pehlivan, E.; Yilmaz, M. Inter. J. Biological Macromol. 2009, 45, 315–320.

    Article  CAS  Google Scholar 

  51. Erdemir, S.; Yilmaz, M. J. Mol. Catal. B: Enzym. 2009, 58, 29–35.

    Article  CAS  Google Scholar 

  52. Ozyilmaz, E.; Sayin, S.; Arslan, M.; Yilmaz, M. Colloid Sur. B: Biointer. 2014, 113, 182–189.

    Article  CAS  Google Scholar 

  53. Akoz, E.; Sayin, S.; Kaplan, S.; Yilmaz, M. Bioprocess Biosyst Eng. 2015, 38, 595–604.

    Article  CAS  Google Scholar 

  54. Pereira, E.B.; De Castro, H.F.; De Moraes, F.F.; Zanin, G.M. Appl. Biochem. Biotechnol. 2001, 93, 739–752.

    Article  Google Scholar 

  55. Erdemir, S.; Yilmaz, M. J. Incl. Phenom. Macrocycl. Chem. 2012, 72, 189–196

    Article  CAS  Google Scholar 

  56. Sayin, S.; Yilmaz, E.; Yilmaz, M. Org. Biomol. Chem. 2011, 9, 4021–4024.

    Article  CAS  Google Scholar 

  57. Ozyilmaz, E.; Sayin, S. Bioprocess Biosyst Eng. 2013, 36, 1803–1806

    Article  CAS  Google Scholar 

  58. Sayin, S.; Akoz, E.; Yilmaz, M. Org. Biomol. Chem. 2014, 12, 6634–6642.

    Article  CAS  Google Scholar 

  59. Ozyilmaz, E.; Bayrakci, M.; Yilmaz, M. Bioorganic Chemistry. 2016, 65, 1–8.

    Google Scholar 

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Correspondence to Mustafa Yilmaz .

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Yilmaz, M., Sayin, S. (2016). Calixarenes in Organo and Biomimetic Catalysis. In: Neri, P., Sessler, J., Wang, MX. (eds) Calixarenes and Beyond. Springer, Cham. https://doi.org/10.1007/978-3-319-31867-7_27

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