Artificial enzymes for the enantioselective Michael-type addition of thiols combining basic catalysis with two- and three-pronged oxyanion hole mimics

Arkivoc

Volumn 2007, Issue 4, 2007, Pages 47-64

  Simón, Luis ^a   Muñiz, Francisco M ^a   Sáez, Silvia ^a   Raposo, César ^a   Morán, Joaquín R ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Chiral catalyst; Conjugated addition; Enzyme like catalysts; Molecular recognition; Oxyanion hole mimics; Xanthone receptors

Indexed keywords

EID: 84962469310     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.405     Document Type: Article

References (59)

1. (a) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887.
2. (b) Nardini, M.; Dijkstra, B. W. Curr. Op. Struct. Biol. 1999, 9, 732.
3. (c) Verschueren, K. H. G.; Seljée, F.; Rozeboom, H. J.; Kalk, K. H.; Dijkstra, B. W. Nature 1993, 363, 693.
4. (d) Harel, M.; Quinn, D. M.; Nair, H. K.; Silman, I.; Sussman, J. L. J. Am. Chem. Soc. 1996, 118, 2340.
5. (e) Hermann, J. C.; Ridder, L.; Mulholland, A. J.; Höltje, H. D. J. Am. Chem. Soc. 2003, 125, 9590.
6. (f) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927.
7. (g) Line, K.; Isupov, M. N.; Littlechild, J. A. J. Mol. Biol. 2004, 338, 519.
8. Thayer, M. M.; Olender, E. H.; Arvai, A. S.; Koike, C. K.; Canestrelli, I. L.; Stewart, J. D.; Benkovic, S. J.; Getzoff, E. D.; Roberts, V. A. J. Mol. Biol. 1999, 291, 329.
9. (a) Bahnson, B. J.; Anderson, V. E.; Petsko, G. A. Biochemistry 2002, 41, 2621.
10. (b) Pawlak, J.; Bahnson, B. J.; Anderson, V. E. Nukleonika 2002, 47 (Suppl. 1), 115.
11. Fulbini, B.; Otero Aldeán, C. Chem. Soc. Rev. 1999, 28, 373.
12. For recent reviews, see for example: (a) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3726.
13. (b) Houk, K. N.; List, B. Acc. Chem. Res., 2004, 37, 487, and next articles in this number of Accounts of Chemical Research.
14. (c) Asymmetric Organocatalysis, from Biomimetic concepts to Applications in Asymmetric Synthesis, Berkessel, A.; Gröguer, H. Wiley-VCH, Weinheim 2005.
15. For recent works and reviews on this field: (a) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
16. (b) Pihko, P. M. Angew. Chem. Int. Ed. 2004, 43, 2062.
17. (c) Fuerst, D. E.; Jacobsen, E. N. 2005, J. Am. Chem. Soc., 127, 8964.
18. (d) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
19. (e) Martín-Portugués, M.; Alcázar, V.; Prados, P.; Mendoza J. Tetrahedron 2002, 58, 2951.
20. (f) Snowden, T. S.; Bisson, A. P.; Anslyn, E. V. Bioorg. Med. Chem. 2001, 9, 2467.
21. (g) Rajaram, S.; Sigman, M. S. Org. Lett. 2005, 7, 5473.
22. (h) Motherwell, W. B.; Bingham, M. J.; Six Y. Tetrahedron 2001, 57, 4663.
23. (i) Zhuang, W.; Poulsen, T. B.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 3284.
24. (j) Ortega-Caballero, F.; Bjerre, J.; Laustsen, L. S.; Bols, M. J. Org. Chem. 2005, 70, 7217.
25. (k) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
26. (l) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc., 2002, 124, 10012.
27. (m) Sigman, M. S.; Vachal, P.; Jacobsen, E. N.; Angew. Chem. Int. Ed. 2000, 39, 1279.
28. (n) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc., 120, 4901-4902, 1998.
29. (o) Curran, D. P.; Kuo, L. H. Tetrahedron Lett. 1995, 36, 6647.
30. (p) Dove, A. P.; Pratt, R. C.; Lohmeifer, B. G. G.; Waymouth, R. M.; Hedrick, J. L.; J. Am. Chem. Soc., 2005, 127, 13798.
31. Hiemstra, H.; Wynberg H. J. Am. Chem. Soc. 1981, 103, 417.
32. Faber, W. S.; Kok, J.; de Lange, B.; Feringa, B.L. Tetrahedron 1994, 50, 4775.
33. (a) Crego, M.; Raposo, C.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1994, 35, 1929.
34. (b) Crego, M.; Raposo, C.; Mussons, M. L.; Berrocal, A.; Caballero, M. C.; Morán, J. R. Heterocycles 1995, 40, 139.
35. (c) Simón, L.; Muñiz, F. M.; Sáez S.; Raposo C.; Sanz, F.; Morán J. R. Helv. Chim. Acta 2005, 88, 1682.
36. Gaussian 98 (Revision A.1.0), Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S. et al Gaussian, Inc., Pittsburgh PA, 1998.
37. (a) Miertus, S.; Scrocco E.; Tomasi J. J. Chem. Phys. 1981, 55, 117.
38. (b) Miertus, S.; Tomasi, J. J. Chem. Phys. 1982, 65, 239.
39. (c) Cances, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.
40. (d) Barone, V.; Cossi, M.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
41. (e) Tomasi, J.; Mennucci B.; Cammi R., Chem. Rev. 2005, 105, 2999.
42. (a) Pardo, L.; Osman, R.; Weinstein, H.; Rabinowitz, J. R. J. Am. Chem. Soc. 1993, 115, 8263.
43. (b) Lin X., Zhao C., Phillips D. L., J.Org.Chem. 2005, 70, 9279.
44. (a) Bruice, P. Y.; Bruice, T. C. J. Am. Chem. Soc. 1974, 96, 5523.
45. (b) Bruice, P. Y.; Bruice, T. C. J. Am. Chem. Soc. 1974, 96, 5533.
46. (c) Adalsteinsson, H.; Bruice, T. C. J. Am. Chem. Soc. 1998, 120, 3440.
47. Breneman, C. M.; Wiberg, K. B. J. Comp. Chem. 1990, 11, 361.
48. Feelding L., Tetrahedron 2000, 56, 6151.
49. Gaussian deconvolution was performed using Mestre-C software. For more information: Cobas, J. C.; Sardina, F. J. Concept. Magn. Reson. 2003, 19A, 80.
50. (a) Takayanagi, H.; Ogura, H. Croat. Chem. Acta 1989, 62, 135.
51. (b) Barth, G.; Voelter, W.; Mosher, H. S.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1970, 92, 875.
52. (a) Humbel, S.; Sieber, S.; Morokuma, K. J. Chem. Phys. 1996, 105, 1959.
53. (b) Maseras, F.; Morokuma, K. J. Comp. Chem. 1995, 16, 1170.
54. (c) Matsubara, T.; Sieber S.; Morokuma, K. Int. J. Quantum Chem. 1996, 60, 1101.
55. (d) Svensson, M.; Humbel, S.; Froese, R. D. J.; Matsubara, T.; Sieber, S.; Morokuma, K. J. Phys. Chem. 1996, 100, 19357.
56. (a) Lo, Y.C.; Lin, S.C.; Shaw, J. F.; Liaw, Y. C. J. Mol. Biol. 2003, 330, 539.
57. (b) Zhu, X.; Larsen, N. A.; Basran, A.; Bruce, N. C.; Wilson, I. A. J. Biol. Chem. 2003, 278, 2008.
58. (c) Nachon, F.; Asojo, O. A.; Borgstahl, G. E. O.; Masson, P.; Lockridge, O. Biochemistry 2005, 44, 1154.
59. (d) Zhang, Y.; Kua, J.; McCammon, J. A. J. Am. Chem. Soc. 2002, 124, 10572.