Experimental determination of the absolute enantioselectivity of an antibody-catalyzed Diels-Alder reaction and theoretical explorations of the origins of stereoselectivity

Journal of the American Chemical Society

Volumn 125, Issue 9, 2003, Pages 2489-2506

  Cannizzaro, Carina E ^a,b   Ashley, Jon A ^a,b   Janda, K D ^a,b   Houk, K N ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS;

ANTIBODIES; BUTADIENE; CATALYSIS; IMMUNIZATION; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL);

QUANTUM THEORY;

ACRYLAMIDE DERIVATIVE; ANTIBODY; CARBAMIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; ENANTIOMER; ENANTIOSELECTIVITY; ENERGY TRANSFER; MOLECULAR DYNAMICS; MOLECULAR MODEL; PREDICTION; QUANTUM MECHANICS; REACTION ANALYSIS; SYNTHESIS; THEORY;

ACRYLAMIDES; AMINO ACID SEQUENCE; ANTIBODIES, CATALYTIC; BUTADIENES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; FERROUS COMPOUNDS; HAPTENS; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS;

EID: 0037420359     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020879d     Document Type: Article

References (112)

1. Recent reviews of enantioselective Lewis acid-catalyzed Diels-Alder reactions: (a) Togni, A.; Venanzi, L. M.; Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima. I., Ed.; VCH: New York, 1993; Chapter 9. (c) Pindur U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741-761. (d) Deloux, L.; Srebnik, M. Chem. Rev, 1993, 93, 763-784. (e) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
2. Recent reviews of enantioselective Lewis acid-catalyzed Diels-Alder reactions: (a) Togni, A.; Venanzi, L. M.; Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima. I., Ed.; VCH: New York, 1993; Chapter 9. (c) Pindur U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741-761. (d) Deloux, L.; Srebnik, M. Chem. Rev, 1993, 93, 763-784. (e) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
3. Recent reviews of enantioselective Lewis acid-catalyzed Diels-Alder reactions: (a) Togni, A.; Venanzi, L. M.; Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima. I., Ed.; VCH: New York, 1993; Chapter 9. (c) Pindur U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741-761. (d) Deloux, L.; Srebnik, M. Chem. Rev, 1993, 93, 763-784. (e) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
4. Recent reviews of enantioselective Lewis acid-catalyzed Diels-Alder reactions: (a) Togni, A.; Venanzi, L. M.; Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima. I., Ed.; VCH: New York, 1993; Chapter 9. (c) Pindur U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741-761. (d) Deloux, L.; Srebnik, M. Chem. Rev, 1993, 93, 763-784. (e) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
5. Recent reviews of enantioselective Lewis acid-catalyzed Diels-Alder reactions: (a) Togni, A.; Venanzi, L. M.; Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. (b) Maruoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima. I., Ed.; VCH: New York, 1993; Chapter 9. (c) Pindur U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741-761. (d) Deloux, L.; Srebnik, M. Chem. Rev, 1993, 93, 763-784. (e) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
6. Ahrendt, K. A.; Borths, C. J.; MacMillan, W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244.
7. Braun, R.; Schuster, F.; Sauer, J. Tetrahedron Lett. 1986, 27, 1285-1288.
8. Colonna, S.; Manfredi, A.; Annunziata, R. Tetrahedron Lett. 1988, 29, 3347-3350.
9. Rao, K. R.; Srinivasan, T, N.; Bhanumathi, N. Tetrahedron Lett. 1990, 31, 5959-5960.
10. (a) Hudlicky, T.; Butora, G.; Fearnley, S. P.; Gum, A. G.; Persichini, P. J., III; Stabile, M. R.; Merola, J. S. J. Chem. Soc., Perkin Trans. 1 1995, 19, 2393-2398.
11. (b) Alvira, E.; Cativiela, C.; Garcia, J. I.; Mayoral, J. A. Tetrahedron Lett. 1995, 36, 2129-2132.
12. (c) Sternbach, D. D.; Rossana, D. M. J. Am. Chem. Soc. 1982, 104, 5853-5854.
13. Kang, J.; Santamaria, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389-7390.
14. (a) Morris, K. N.; Tarasow, T. M.; Julin, C. M.; Simons, S. L.; Hilvert, D.; Gold, L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 13028-13032.
15. (b) Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167-176.
16. (c) Tarasow, T. M.; Eaton, B. E. J. Am. Chem. Soc. 2000, 122, 1015-1021.
17. Ichihara, A.; Oikawa, H. In Comprehensive Natural Products Chemistry; Sankawa, U., Ed.; Barton, D., Nakanishi, K., Met-Cohn, O., Series Eds.; Polyketides and Other Secondary Metabolites, Vol. 1; Elsevier: New York, 1999; pp 367-408.
18. (a) Pohnert, G. ChemBioChem 2001, 2, 873-875.
19. (b) Auclair, K.; Sutherland, A.; Kennedy, J.; Witter, D. J.; Van den Heever, J. P.; Hutchinson, C. R. Vederas, J. C. J. Am. Chem. Soc. 2000, 122, 11519-11520.
20. (c) Hutchinson, C. R.; Kennedy, J.; Park, C.; Kendrew, S.; Auclair, K.; Vederas, J. Antonie van Leewenhoek 2000, 78, 287-295.
21. (a) Oikawa, H.; Katayama, K.; Suzuki, Y.; Ichihara, A. J. Chem. Soc., Chem. Commun. 1995, 1321-1322.
22. (b) Oikawa, H.; Kobayashi, T.; Katayama, K.; Suzuki, Y.; Ichihara, A. J. Org. Chem. 1998, 63, 8748-8756.
23. (c) Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Biochim. Biophys. Acta 1998, 1384, 387-395.
24. (d) Oikawa, H.; Suzuki, Y.; Katayama, K.; Naya, A.; Sakano, C.; Ichihara, A. J. Chem. Soc., Perkin Trans. 1 1999. 1225-1232.
25. (a) Watanabe, K; Mie, T.; Ichihara, A.; Oikawa, H.; Honma, M. J. Biol. Chem. 2000. 78. 287-295. (b) For a recent review on Diels-Alderases: Pohnert, G. ChemBioChem. 2001, 2, 873-875.
26. (a) Watanabe, K; Mie, T.; Ichihara, A.; Oikawa, H.; Honma, M. J. Biol. Chem. 2000. 78. 287-295. (b) For a recent review on Diels-Alderases: Pohnert, G. ChemBioChem. 2001, 2, 873-875.
27. (a) Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M. M. J. Am. Chem. Soc. 1989, 111, 1, 9261-9262.
28. (b) Braisted, A. C.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430.
29. (c) Suckling, C. J.; Tedford, M. C.; Bence, L. M.; Irvine, J. I.; Stimson, W. H. J. Chem. Soc., Perkin Trotas. 1 1993, 1925.
30. (d) Gouvemeur, V. E.; Houk, K. N.; de Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lemer, R. A. Science 1993, 262. 204-208.
31. (e) Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
32. (f) Meekel, A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571-572.
33. (g) Resmini, M.; Meekel, A. P.; Pandit, U. K. Pure Appl. Chem. 1996, 68, 2025-2028.
34. (a) Wentworth, P., Jr.; Janda, K. D. Cell Biochem. Biophys. 2001, 35, 63-87.
35. (b) Tremblay, M. R.; Dickerson, T. J.; Janda, K. D. Adv. Synth. Catal. 2001, 343, 577-585 and references therein.
36. (c) Schultz, P. G.; Lerner, R. A. Science 1995, 269, 1835.
37. (d) Stewart, J. D.; Benkovic, S. J. Nature 1995, 375, 388-391.
38. (e) Keinan, E.; Lemer, R. A. Isr. J. Chem. 1996, 36, 113-119.
39. (f) Morrison, J. D., Ed. Chiral Catalysis: Asymmetric Synthesis, Vol. 5; Academic Press: New York, 1985.
40. Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
41. Huanh, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2000, 122, 7843-7844.
42. Heine, A.; Stura, E. A.; Yli-Kauhaluorna, J. T.; Gao, C.; Deng, Q.; Beno, B. R.; Houk, K. N.; Janda, K. D. and Wilson, I. A. Science 1998, 279, 1934-1940.
43. Overman, L. E.; Taylor, G. F.; Petty, C. B.; Jessup, P. J. J. Org. Chem. 1978, 43 2164.
44. Evans, D. A.; Chapman, K. T.; Hung, D. T.; Kawaguchi, A. T. Angew. Chem., Int. Ed. Engl. 1987, 26, 1184-1186.
45. Jessup, P. J.; Petty, C. B.; Roos, J.; Overman, L. E. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 95.
46. Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517-5518.
47. Newman, M. S.; Kutner, A. J. Am. Chem. Soc. 1951, 73, 4199-4204.
48. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
49. Mathre, D. J.; Ho, G.-J. J. Org. Chem. 1995, 60, 2271-2273.
50. Gawley, R. E.; Aubé J. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996; p 263.
51. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144.
52. Jackson, A. E.; Johnstone, R. A. W. Synthesis 1976, 685-687.
53. Meienhofer, J.; Kuromizu, K. Tetrahedron Lett. 1974, 37, 3259-3262.
54. ElAmin, B.; Anantharamaiah, G. M.; Royer, G. P.; Means, G. E. J. Org. Chem. 1979, 44, 3442-3444.
55. Davies, S. G.; Ichihara, O.; Lenoir, I.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1411-1415.
56. Jung, M. E.; Dámico, D. C. J. Am. Chem. Soc. 1995, 117, 7379-7388.
57. Nohira, H.; Ehara, K.; Miyashita, A. Bull. Chem. Soc. Jpn. 1970, 43, 2230-2233.
58. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
59. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
60. Wong, M. W. Chem. Phys. Lett. 1996, 256, 391-399.
61. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
62. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19, 1639-1662.
63. Pearlman, D. A.; Case, D. A.; Caldwell, J. W.; Ross, W. S.; Cheathman, T. E., III; DeBolt, S.; Ferguson, D.; Seibel, G.; Kollman, P. Comput. Phys. Commun. 1995, 91, 1-41.
64. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M., Jr.; Ferguson D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. J. Am. Chem. Soc. 1995, 117, 5179-5197.
65. Sustmann, R. Tetrahedron Lett. 1971, 2721-2724.
66. Sustmann, R.; Shubert, R. Angew. Chem. Int. Ed. Engl. 1972, 11, 840.
67. Vargas, R.; Garza, J.; Dixon, D. A.; Hay, B. P. J. Am. Chem. Soc. 2000, 122, 4750-4755.
68. InsightII/Discover: Biosyn/Molecular Simulations Inc.: San Diego, CA.
69. Wedemayer, G. J.; Patten, P. A.; Wang, L. H.; Schultz, P. G.; Stevens, R. C. Science 1997, 276, 1665-1669.
70. Amit, A. G.; Mariuzza, R. A.; Phillips, S. E. V.; Poljak, R. J. Science 1986, 233, 747.
71. (a) Stewart, W. E.; Siddall, T. H., III. Chem. Rev. 1970, 70, 517.
72. (b) Oki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry; VCH: Deerfield Beach, 1985; Chapter 2.
73. (a) Drakenberg, T.; Dahlqvist, K.-I.; Forsen, S. J. Phys. Chem. 1972, 76, 2178-2183.
74. (b) Eberhardt, E. S.; Loh, S. N.; Hinck, A. P.; Raines, R. T. J. Am. Chem. Soc. 1992, 114, 5437-5439.
75. Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 2426-2427.
76. Van der Werf, S.; Olijnsma, T.; Engberts, J. B. F. N. Tetrahedron Lett. 1967, 689-693.
77. (a) Review: Jone, G. I. L.; Owen, N. L. J. Mol. Struct. 1973, 18, 1.
78. (b) Grindley, T. B. Tetrahedron Lett. 1982, 23, 1757-1760.
79. Nelson, M. R.; Borkman, R. F. J. Mol. Struct. (THEOCHEM) 1998, 432, 247-255.
80. Karabatsos, G. J.; His, N.; Orzech, C. E., Jr. Tetrahedron Lett. 1966, 4639-4643.
81. (a) Abraham, R. J.; Bakke, J. M. Tetrahedron 1978, 34, 2947-2951.
82. (b) Mons, M.; Robertson, E. G.; Simons, J. P. J. Phys. Chem. A 2000, 104, 1430-1437.
83. Mesecar, A. D.; Koshland, D. E., Jr. Nature 2000, 403, 614-615.
84. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. J. Comput. Phys. 1997, 23, 327-341.
85. Berensen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684.
86. Shabat, D.; Shulman, H.; Itzhaky, H.; Reymond, J.-L.; Keinan, E. J. Chem. Soc., Chem. Commun. 1998, 16, 1759-1760.
87. Gill, T. J., III; Kunz, H. W.; Papermaster, D. S. J. Biol. Chem. 1967, 242, 3308.
88. Jenks, W. P. Catalysis in Chemistry and Immunology; McGraw-Hill: New York, 1969; p 288.
89. (a) Janda, K. D.; Benkovic, S. J.; Lemer, R. A. Science 1989, 244, 437-440.
90. (b) Nakatani, T.; Hiratake, J.; Shinzaki, A.; Umeshita, R.; Suzuki, T.; Nishioka, T.; Nakajima, H.; Oda, J. Tetrahedron Lett. 1993, 34, 4945-4948.
91. (c) Tanaka, F.; Kinoshita, K.; Tanimura, R.; Fujii, I. J. Am. Chem. Soc. 1996, 118, 2332-2339.
92. (a) Cochran, A. G. J. Am. Chem. Soc. 1991, 113, 6670-6672.
93. (b) Martin, M. T.; Angeles, T. S.; Sugasawara, R.; Aman, N. I.; Napper, A. D.; Darsley, M. J.; Sanchez, R. I.; Booth, P.; Titmas, R. C. J. Am. Chem. Soc. 1994, 116, 6508-6512.
94. (a) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069.
95. (b) Lo, C.-H. L.; Wentworth, P.; Jung, K. W.; Yoon, J.; Ashley, J. A.; Janda, K. D. J. Am. Chem. Soc. 1997, 119, 10251-10252.
96. For both the CPY and CPQ immunizations, 100νg (of a 5 mg/mL KLH conjugate) per mouse per injection were used. Four mice were immunized each with 100 μg CPY-KLH (or CPQ-KLH) in 200 μL RIB[adjuvant intraperitoneally. Two weeks later the mice were boosted again with another 100 μg, The mice were bled I week later, and the titers were determined by ELISA. After I month, a final injection with 50 μg of hapten-KLH in 100 μL PBS was performed intravenously in the tail vein. Three days later the spleen was removed for fusion.
97. Schechter, I.; Sela, M. Biochemistry 1967, 6, 897.
98. Mader, M. M.; Bartlett, P. A. Chem. Rev. 1997, 97. 1281-1301.
99. (a) Benedetti, F.; Berti, F.; Flego, M.; Resmini, M.; Bastiani, E. Anal. Biochemistry 1998, 256, 67-73.
100. (b) Shuhnan, H.; Eberhard, A.; Eberhard, C.; Ulitzur, S.; Keinan, E. Bioorg. Med. Chem. Lett. 2000, 10, 2353-2356 and references therein.
101. (a) Lee, J. K.; Houk, K. N. Science 1997, 276. 942-945.
102. (b) Daopin, S.; Anderson D. E.; Baase, W. A.; Dalhquist, F. W.; Matthews, B. W. Biochemistry 1991, 30, 11521.
103. Burton, D. R. Acc. Chem. Res. 1993, 26, 405-411.
104. (a) Burnet, F. M. In The Clonal Selection Theory of Acquired Immunity; Vanderbilt University Press: Nashville, TN, 1959; p 53.
105. (b) Talmage, D. W. Science 1959, 129, 1649.
106. (c) Lederberg, J. Science 1959, 129, 1649.
107. (d) Tonegawa, S. Nature 1983, 302, 575.
108. (e) French, D. L.; Laskov, R.; Scharff, M. D. Science 1989, 244, 1152.
109. Romesberg, F. E.; Spiller, B.; Schultz, P. G.; Stevens, R. C. Science 1998. 279, 1929-1933.
110. Yin, J.; Mundorff, E. C.; Yang, P. L.; Wendt, K. U.; Hanway, D.; Stevens, R. C.; Schultz, P. G. Biochemistry 2001, 40, 10764-10773.
111. Ulrich, H. D.; Schultz, P. G. J. Mol. Biol. 1998, 275, 95-111.
112. Tantillo, D. J.; Houk, K. N. Chem. Biol. 2001, 535-545.