Exploring the aldol reaction using catalytic antibodies and "on water" organocatalysts from QM/MM calculations

Journal of the American Chemical Society

Volumn 136, Issue 1, 2014, Pages 147-156

  Armacost, Kira ^a   Acevedo, Orlando ^a  

^a AUBURN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ANTIBODIES; ELECTRONIC STABILIZATION; ELECTROSTATIC STABILIZATION; FREE ENERGY PERTURBATION; MONTE CARLO CALCULATION; SOLVENT ACCESSIBILITY; SPECIFIC HYDROGEN BONDINGS; TRANSITION STRUCTURES;

ACETONE; AMIDES; CATALYSTS; CONDENSATION REACTIONS; EMULSIFICATION; HYDROGEN BONDS; OXYGEN; STABILIZATION;

ANTIBODIES;

ACETONE; AMINOALCOHOL; ANTIBODY 33F12; ASPARAGINE; BENZALDEHYDE; CATALYTIC ANTIBODY; ENAMINE; SERINE; TRYPTOPHAN; TYROSINE; UNCLASSIFIED DRUG; WATER;

ALDOL REACTION; ARTICLE; CALCULATION; CATALYSIS; CATALYST; CLAISEN REARRANGEMENT; CONFORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; EMULSION; ENANTIOSELECTIVITY; HYDROGEN BOND; HYDROPHOBICITY; MONTE CARLO METHOD; NONAQUEOUS PHASE LIQUID; ORGANOCATALYST; PHASE TRANSITION; PROTON TRANSPORT; REACTION ANALYSIS;

ACETONE; ALDEHYDES; ANTIBODIES, CATALYTIC; BENZALDEHYDES; CATALYSIS; CATALYTIC DOMAIN; MODELS, CHEMICAL; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM; WATER;

EID: 84892147377     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja405614p     Document Type: Article

References (79)

1. List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395-2396
2. List, B. Tetrahedron 2002, 58, 5573-5590
3. Notz, W.; Tanaka, F.; Barbas, C. F., III Acc. Chem. Res. 2004, 37, 580-591
4. List, B. Acc. Chem. Res. 2004, 37, 548-557
5. Bock, D. A.; Lehmann, C. W.; List, B. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20636-20641
6. Allemann, C.; Gordillo, R.; Clemente, F. R.; Cheong, P. H.-Y.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558-569
7. Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. 1971, 10, 496-497
8. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621
9. Cohen, N. Acc. Chem. Res. 1976, 9, 412-417
10. Bisai, V.; Bisai, A.; Singh, V. K. Tetrahedron 2012, 68, 4541-4580
11. Barbas, C. F., III Angew. Chem., Int. Ed. 2008, 47, 42-47
12. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138-6171
13. Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638-4660
14. MacMillan, D. W. C. Nature 2008, 455, 304-308
15. Zhao, J. H. L.; Jiang, J.; Tang, Z.; Cun, L.; Gong, L. Tetrahedron Lett. 2008, 49, 3372-3375
16. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569
17. Raj, M.; Vishnumaya; Ginotra, S. K.; Singh, V. K. Org. Lett. 2006, 8, 4097-4099
18. Dziedzic, P. Z. W.; Hafren, J.; Cordova, A. Org. Biomol. Chem. 2006, 4, 38-40
19. Tang, Z.; Yang, Z.-H.; Chen, X.-H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. J. Am. Chem. Soc. 2005, 127, 9285-9289
20. Tang, Z.; Jiang, F.; Cui, X.; Gong, L.; Mi, A.; Jiang, Y.; Wu, Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755-5760
21. Machajewski, T. D.; Wong, C. Angew. Chem., Int. Ed. 2000, 39, 1352-1374
22. Vishnumaya, M. R.; Singh, V. K. J. Org. Chem. 2009, 74, 4289-4297
23. Maya, V.; Raj, M.; Singh, V. K. Org. Lett. 2007, 9, 2593-2595
24. Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263
25. Ribas-Arino, J.; Carvajal, M. A.; Chaumont, A.; Masia, M. Chem.-Eur. J. 2012, 18, 15868-15874
26. Tang, G.; Hu, X.; Altenbach, H. J. Tetrahedron Lett. 2011, 52, 7034-7037
27. Bhowmick, S.; Bhowmick, K. C. Tetrahedron Asymmetry 2011, 22, 1945-1979
28. Aratake, S.; Itoh, T.; Okano, T.; Usui, T.; Shoji, M.; Hayashi, Y. Chem. Commun. 2007, 2524-2526
29. Guizzetti, S.; Benaglia, M.; Raimondi, L.; Celentano, G. Org. Lett. 2007, 9, 1247-1250
30. Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., III J. Am. Chem. Soc. 2006, 128, 734-735
31. Hayashi, Y.; Sumiya, T.; Takahashi, J.; Gotoh, H.; Urushima, T.; Shoji, M. Angew. Chem., Int. Ed. 2006, 45, 958-961
32. Hayashi, Y.; Aratake, S.; Okano, T.; Takahashi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2006, 45, 5527-5529
33. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275-3279
34. Narayan, S.; Fokin, V. V.; Sharpless, K. B. In Organic Reactions in Water; Blackwell Publishing Ltd.: Oxford, UK, 2007; pp 350-365.
35. Hayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 8103-8104
36. Klijn, J. E.; Engberts, J. B. F. N. Nature 2005, 435, 746-747
37. Wagner, J.; Lerner, R. A.; Barbas, C. F., III Science 1995, 270, 1797-1800
38. Barbas, C. F., III; Heine, A.; Zhong, G.; Hoffmann, T.; Gramatikova, S.; Björnestedt, R.; List, B.; Anderson, J.; Stura, E. A.; Wilson, I. A.; Lerner, R. A. Science 1997, 278, 2085-2092
39. Zhong, G.; Hoffmann, T.; Lerner, R. A.; Danishefsky, S.; Barbas, C. F., III J. Am. Chem. Soc. 1997, 119, 8131-8132
40. Hoffmann, T.; Zhong, G.; List, B.; Shabat, D.; Anderson, J.; Gramatikova, S.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 1998, 120, 2768-2779
41. Bertelsen, S.; Jørgensen, K. A. Chem. Soc. Rev. 2009, 38, 2178-2189
42. Zhu, X.; Tanaka, F.; Lerner, R. A.; Barbas, C. F., III; Wilson, I. A. J. Am. Chem. Soc. 2009, 131, 18206-18207
43. Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273-11283
44. Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479
45. Clemente, F. R.; Houk, K. N. Angew. Chem., Int. Ed. 2004, 43, 5766-5768
46. Clemente, F. R.; Houk, K. N. J. Am. Chem. Soc. 2005, 127, 11294-11302
47. Zhang, X.; Houk, K. N. J. Org. Chem. 2005, 70, 9712-9716
48. Zhao, Q.; Lam, Y.-h.; Kheirabadi, M.; Xu, C.; Houk, K. N.; Schafmeister, C. E. J. Org. Chem. 2012, 77, 4784-4792
49. Cheong, P. H.-Y.; Legault, C. Y.; Um, J. M.; Çelebi- Ölçüm, N.; Houk, K. N. Chem. Rev. 2011, 111, 5042-5137
50. Zhu, H.; Clemente, F. R.; Houk, K. N.; Meyer, M. P. J. Am. Chem. Soc. 2009, 131, 1632-1633
51. Allemann, C.; Uma, J. M.; Houk, K. N. J. Mol. Catal. A: Chem. 2010, 324, 31-38
52. Zhu, X.; Tanaka, F.; Hu, Y.; Heine, A.; Fuller, R.; Zhong, G.; Olson, A. J.; Lerner, R. A.; Barbas, C. F., III; Wilson, I. A. J. Mol. Biol. 2004, 343, 1269-1280
53. Jorgensen, W. L.; Tirado-Rives, J. J. Comput. Chem. 2005, 26, 1689-1700
54. Acevedo, O.; Jorgensen, W. L. Acc. Chem. Res. 2010, 43, 142-151
55. Allen, C.; Sambasivarao, S. V.; Acevedo, O. J. Am. Chem. Soc. 2013, 135, 1065-1072
56. Acevedo, O.; Armacost, K. J. Am. Chem. Soc. 2010, 132, 1966-1975
57. Sheppard, A. N.; Acevedo, O. J. Am. Chem. Soc. 2009, 131, 2530-2540
58. Acevedo, O. J. Phys. Chem. B 2009, 113, 15372-15381
59. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926-935
60. Kurtz, S. S., Jr.; Wikingsson, A. E.; Camin, D. L.; Thompson, A. R. J. Chem. Eng. Data 1965, 10, 330-334
61. Chickos, J. S.; Acree, W. E. J. Phys. Chem. Ref. Data 2003, 32, 519-878
62. Thompson, J. D.; Cramer, C. J.; Truhlar, D. G. J. Comput. Chem. 2003, 24, 1291-1304
63. Vilseck, J. Z.; Sambasivarao, S. V.; Acevedo, O. J. Comput. Chem. 2011, 32, 2836-2842
64. Kaminski, G. A.; Friesner, R. A.; Tirado-Rives, J.; Jorgensen, W. L. J. Phys. Chem. B 2001, 105, 6474-6487
65. Tubert-Brohman, I.; Acevedo, O.; Jorgensen, W. L. J. Am. Chem. Soc. 2006, 128, 16904-16913
66. Sambasivarao, S. V.; Acevedo, O. J. Chem. Theory Comput. 2009, 5, 1038-1050
67. Reymond, J.-L. J. Mol. Catal. B: Enzym. 1998, 5, 331-337
68. Zhong, G.; Shabat, D.; List, B.; Anderson, J.; Sinha, S. C.; Lerner, R. A.; Barbas, C. F., III Angew. Chem., Int. Ed. 1998, 37, 2481-2484
69. Zhong, G.; Lerner, R. A.; Barbas, C. F., III Angew. Chem., Int. Ed. 1999, 38, 3738-3741
70. Turner, J. M.; Bui, T.; Lerner, R. A.; Barbas, C. F., III; List, B. Chem.-Eur. J. 2000, 6, 2772-2774
71. Tanaka, F.; Barbas, C. F., III J. Immunol. Methods 2002, 269, 67-79
72. Karlstrom, A.; Zhong, G.; Rader, C.; Larsen, N. A.; Heine, A.; Fuller, R.; List, B.; Tanaka, F.; Wilson, I. A.; Barbas, C. F., III; Lerner, R. A. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 3878-3883
73. Arnó, M.; Domingo, L. R. Org. Biomol. Chem. 2003, 1, 637-643
74. Alexandrova, A. N.; Röthlisberger, D.; Baker, D.; Jorgensen, W. L. J. Am. Chem. Soc. 2008, 103, 15907-15915
75. Röthlisberger, D.; Khersonsky, O.; Wollacott, A. M.; Jiang, L.; DeChancie, J.; Betker, J.; Gallaher, J. L.; Althoff, E. A.; Zanghellini, A.; Dym, O.; Albeck, S.; Houk, K. N.; Tawfik, D. S.; Baker, D. Nature 2008, 453, 190-195
76. Jiang, L.; Althoff, E. A.; Clemente, F. R.; Doyle, L.; Röthlisberger, D.; Zanghellini, A.; Gallaher, J. L.; Betker, J. L.; Tanaka, F.; Barbas, C. F., III; Hilvert, D.; Houk, K. N.; Stoddard, B. L.; Baker, D. Science 2008, 319, 1387-1391
77. Frisch, M. J., revision B.01; Gaussian, Inc.: Wallingford, CT, 2009; full reference given in SI.
78. Schmid, M. B.; Zeitler, K.; Gschwind, R. M. Chem. Sci. 2011, 2, 1793-1803
79. DeChancie, J.; Acevedo, O.; Evanseck, J. D. J. Am. Chem. Soc. 2004, 126, 6043-6047