Antibody-catalysis of a bimolecular asymmetric 1,3-dipolar cycloaddition reaction [15]

Journal of the American Chemical Society

Volumn 122, Issue 13, 2000, Pages 3244-3245

  Toker, Jonathan D ^a   Wentworth Jr , Paul ^a   Hu, Yunfeng ^b   Houk, K N ^b   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXAZOLE DERIVATIVE;

CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; KINETICS; LETTER; MOLECULAR MODEL; STEREOCHEMISTRY;

EID: 0034607299     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994423g     Document Type: Letter

References (40)

1. One bimolecular pericyclic reaction catalyzed by antibodies has been reported: the Diels-Alder reaction. For reviews, see: (a) Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth, P., Jr. Adv. Phys. Org. Chem. 1998, 31, 249-392. (b) Wentworth, P., Jr.; Janda, K. D. Curr. Opin. Chem. Biol. 1998, 2, 138-144. (c) Hilvert D.; Hill, K. W. Methods Enzymol. 1991, 203, 352-369. For research articles, see: (d) Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261-9262. (e) Braisted, A. C.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430-7431. (f) Gouverneur, V. E.; Houk, K. N.; De Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204-208. (g) Meekel, A. A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571-572. (h) Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
2. One bimolecular pericyclic reaction catalyzed by antibodies has been reported: the Diels-Alder reaction. For reviews, see: (a) Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth, P., Jr. Adv. Phys. Org. Chem. 1998, 31, 249-392. (b) Wentworth, P., Jr.; Janda, K. D. Curr. Opin. Chem. Biol. 1998, 2, 138-144. (c) Hilvert D.; Hill, K. W. Methods Enzymol. 1991, 203, 352-369. For research articles, see: (d) Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261-9262. (e) Braisted, A. C.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430-7431. (f) Gouverneur, V. E.; Houk, K. N.; De Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204-208. (g) Meekel, A. A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571-572. (h) Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
3. One bimolecular pericyclic reaction catalyzed by antibodies has been reported: the Diels-Alder reaction. For reviews, see: (a) Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth, P., Jr. Adv. Phys. Org. Chem. 1998, 31, 249-392. (b) Wentworth, P., Jr.; Janda, K. D. Curr. Opin. Chem. Biol. 1998, 2, 138-144. (c) Hilvert D.; Hill, K. W. Methods Enzymol. 1991, 203, 352-369. For research articles, see: (d) Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261-9262. (e) Braisted, A. C.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430-7431. (f) Gouverneur, V. E.; Houk, K. N.; De Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204-208. (g) Meekel, A. A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571-572. (h) Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
4. One bimolecular pericyclic reaction catalyzed by antibodies has been reported: the Diels-Alder reaction. For reviews, see: (a) Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth, P., Jr. Adv. Phys. Org. Chem. 1998, 31, 249-392. (b) Wentworth, P., Jr.; Janda, K. D. Curr. Opin. Chem. Biol. 1998, 2, 138-144. (c) Hilvert D.; Hill, K. W. Methods Enzymol. 1991, 203, 352-369. For research articles, see: (d) Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261-9262. (e) Braisted, A. C.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430-7431. (f) Gouverneur, V. E.; Houk, K. N.; De Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204-208. (g) Meekel, A. A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571-572. (h) Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
5. One bimolecular pericyclic reaction catalyzed by antibodies has been reported: the Diels-Alder reaction. For reviews, see: (a) Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth, P., Jr. Adv. Phys. Org. Chem. 1998, 31, 249-392. (b) Wentworth, P., Jr.; Janda, K. D. Curr. Opin. Chem. Biol. 1998, 2, 138-144. (c) Hilvert D.; Hill, K. W. Methods Enzymol. 1991, 203, 352-369. For research articles, see: (d) Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261-9262. (e) Braisted, A. C.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430-7431. (f) Gouverneur, V. E.; Houk, K. N.; De Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204-208. (g) Meekel, A. A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571-572. (h) Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
6. One bimolecular pericyclic reaction catalyzed by antibodies has been reported: the Diels-Alder reaction. For reviews, see: (a) Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth, P., Jr. Adv. Phys. Org. Chem. 1998, 31, 249-392. (b) Wentworth, P., Jr.; Janda, K. D. Curr. Opin. Chem. Biol. 1998, 2, 138-144. (c) Hilvert D.; Hill, K. W. Methods Enzymol. 1991, 203, 352-369. For research articles, see: (d) Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261-9262. (e) Braisted, A. C.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430-7431. (f) Gouverneur, V. E.; Houk, K. N.; De Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204-208. (g) Meekel, A. A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571-572. (h) Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
7. One bimolecular pericyclic reaction catalyzed by antibodies has been reported: the Diels-Alder reaction. For reviews, see: (a) Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth, P., Jr. Adv. Phys. Org. Chem. 1998, 31, 249-392. (b) Wentworth, P., Jr.; Janda, K. D. Curr. Opin. Chem. Biol. 1998, 2, 138-144. (c) Hilvert D.; Hill, K. W. Methods Enzymol. 1991, 203, 352-369. For research articles, see: (d) Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261-9262. (e) Braisted, A. C.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430-7431. (f) Gouverneur, V. E.; Houk, K. N.; De Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204-208. (g) Meekel, A. A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571-572. (h) Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
8. One bimolecular pericyclic reaction catalyzed by antibodies has been reported: the Diels-Alder reaction. For reviews, see: (a) Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth, P., Jr. Adv. Phys. Org. Chem. 1998, 31, 249-392. (b) Wentworth, P., Jr.; Janda, K. D. Curr. Opin. Chem. Biol. 1998, 2, 138-144. (c) Hilvert D.; Hill, K. W. Methods Enzymol. 1991, 203, 352-369. For research articles, see: (d) Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261-9262. (e) Braisted, A. C.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 7430-7431. (f) Gouverneur, V. E.; Houk, K. N.; De Pascual-Teresa, B.; Beno, B.; Janda, K. D.; Lerner, R. A. Science 1993, 262, 204-208. (g) Meekel, A. A. P.; Resmini, M.; Pandit, U. K. J. Chem. Soc., Chem. Commun. 1995, 571-572. (h) Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
9. (a) Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; Taylor, E. C., Weissberger, A., Eds.; John Wiley & Sons: New York, 1984.
10. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909.
11. (c) Ho, T.-L. Tandem Organic Reactions; John Wiley and Sons: New York, 1992.
12. No naturally occurring biocatalyst for a 1,3-dipolar cycloaddition reaction has yet been either identified, isolated, or characterized. A recent report has outlined that Baker's yeast extract (Saccharomyces cerevisiae) can catalyze this reaction under certain conditions; (a) Rama Rao, K.; Nageswar, Y. V. D.; Sampathkumar, H. M. J. Chem. Soc., Perkin Trans. 1 1990, 3199. (b) Rama Rao, K.; Nageswar, Y. V. D.; Bhanumathi, N.; Srinivasan, T. N. Ind. J. Chem. 1994, 33B, 171-172.
13. No naturally occurring biocatalyst for a 1,3-dipolar cycloaddition reaction has yet been either identified, isolated, or characterized. A recent report has outlined that Baker's yeast extract (Saccharomyces cerevisiae) can catalyze this reaction under certain conditions; (a) Rama Rao, K.; Nageswar, Y. V. D.; Sampathkumar, H. M. J. Chem. Soc., Perkin Trans. 1 1990, 3199. (b) Rama Rao, K.; Nageswar, Y. V. D.; Bhanumathi, N.; Srinivasan, T. N. Ind. J. Chem. 1994, 33B, 171-172.
14. (a) Houk, K. N.; Yamaguchi, K. Theory of 1,3-Dipolar Cycloadditions In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley and Sons: New York, 1984; Vol. 2, pp 407-450.
15. (b) Houk, K. N.; Gonzalez, J.; Li, Y. Arc. Chem. Res. 1995, 28, 81-90.
16. (a) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 633-636.
17. (b) Firestone, R. A. J. Org. Chem. 1968, 33, 2285.
18. (a) Morao, I.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1997, 62, 7033-7036.
19. (b) Morao, I.; Cossío, F. P. J. Org. Chem. 1999, 64, 1868-1874.
20. For reports of antibodies as "entropic traps", see: (a) Janda, K. D.; Lerner, R. A.; Tramontano, A. J. Am. Chem. Soc. 1988, 110, 4835. (b) Jackson, D. Y.; Jacobs, J. W.; Sugasawara, R.; Reich, S. H.; Bartlett, P. A.; Schultz, P. G. J. Am. Chem. Soc. 1988, 110, 4841-4842. (c) Hilvert, D.; Nared, K. D. J. Am. Chem. Soc. 1988, 110, 5593-5594. (d) Napper, A. D.; Benkovic, S. J.; Tramontano, A.; Lerner, R. A. Science 1987, 237, 1041-1043.
21. For reports of antibodies as "entropic traps", see: (a) Janda, K. D.; Lerner, R. A.; Tramontano, A. J. Am. Chem. Soc. 1988, 110, 4835. (b) Jackson, D. Y.; Jacobs, J. W.; Sugasawara, R.; Reich, S. H.; Bartlett, P. A.; Schultz, P. G. J. Am. Chem. Soc. 1988, 110, 4841-4842. (c) Hilvert, D.; Nared, K. D. J. Am. Chem. Soc. 1988, 110, 5593-5594. (d) Napper, A. D.; Benkovic, S. J.; Tramontano, A.; Lerner, R. A. Science 1987, 237, 1041-1043.
22. For reports of antibodies as "entropic traps", see: (a) Janda, K. D.; Lerner, R. A.; Tramontano, A. J. Am. Chem. Soc. 1988, 110, 4835. (b) Jackson, D. Y.; Jacobs, J. W.; Sugasawara, R.; Reich, S. H.; Bartlett, P. A.; Schultz, P. G. J. Am. Chem. Soc. 1988, 110, 4841-4842. (c) Hilvert, D.; Nared, K. D. J. Am. Chem. Soc. 1988, 110, 5593-5594. (d) Napper, A. D.; Benkovic, S. J.; Tramontano, A.; Lerner, R. A. Science 1987, 237, 1041-1043.
23. For reports of antibodies as "entropic traps", see: (a) Janda, K. D.; Lerner, R. A.; Tramontano, A. J. Am. Chem. Soc. 1988, 110, 4835. (b) Jackson, D. Y.; Jacobs, J. W.; Sugasawara, R.; Reich, S. H.; Bartlett, P. A.; Schultz, P. G. J. Am. Chem. Soc. 1988, 110, 4841-4842. (c) Hilvert, D.; Nared, K. D. J. Am. Chem. Soc. 1988, 110, 5593-5594. (d) Napper, A. D.; Benkovic, S. J.; Tramontano, A.; Lerner, R. A. Science 1987, 237, 1041-1043.
24. -1 lower than for formation of the 4-isomer in water (energies obtained with B3LYP/6-31+G* calculations).
25. Hapten 4 was synthesized in three steps from 2-nitrobenzoic acid and will be reported elsewhere.
26. (a) Harlow, E.; Lane, D. Antibodies: A Laboratory Manual; Cold Spring Harbor Lab: New York, 1988.
27. Assays were performed in aqueous buffer [50 mM MES (pH 6.5), 50 mM NaCl, 4% v/v DMSO] at 4 °C unless otherwise stated. See Supporting Information.
28. When programming antibody-catalysts for bimolecular associative processes the risk of product inhibition is a concern. The planar core of hapten 4 was considered to be sufficiently different from the isoxazoline ring of 3a and 3b such that product inhibition should be obviated.
29. Segel, I. H. Enzyme Kinetics; John Wiley and Sons: New York, 1975.
30. (a) Cleland, W. W. Biochim. Biophys. Acta 1963, 67, 104-105.
31. (b) Cleland, W. W. Steady-State Kinetics; Boyer, P. D., Ed.; Academic Press: New York, 1970; Vol' 2, pp 1-65.
32. Van Mersbergen, D.; Wijnen, J. W.; Engberts, J. B. F. N. J. Org. Chem. 1998, 63, 8801-8805.
33. 4); unit cell parameters: a = 6.7566 (12) Å a = 90° b = 9.1409 (11) Å β= 90° c = 22.481 (2) Å γ = 90°; temp. 296 K.; Z = 4. (b) The ee and absolute stereochemistry of the 29G12-catalyzed 1,3-DPC was determined by chiral HPLC and X-ray crystallography (ref 16a), respectively. See Supporting Information.
34. Determined from Arrhenius plots.
35. For reports of medium effects in 1,3-DPC reactions see [(a) Beltrame, P.; Sartirana, P.; Vintani, C. J. Chem. Soc. (B) 1971, 814. (b) Inoue, Y.; Araki, K.; Shiraishi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3079-3083. (c) Wijnen, J. W.; Steiner, R. A.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 5389-5390]. Bovine serum albumin (BSA) does not catalyze the reaction between 1 and 2 [for reports of BSA-catalysis of medium-sensitive reactions, see: (a) Kikuchi, K.; Thorn, S. N.; Hilvert, D. J. Am. Chem. Soc. 1996, 118, 8184-8185. (b) Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. Nature 1996, 353, 60-63].
36. For reports of medium effects in 1,3-DPC reactions see [(a) Beltrame, P.; Sartirana, P.; Vintani, C. J. Chem. Soc. (B) 1971, 814. (b) Inoue, Y.; Araki, K.; Shiraishi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3079-3083. (c) Wijnen, J. W.; Steiner, R. A.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 5389-5390]. Bovine serum albumin (BSA) does not catalyze the reaction between 1 and 2 [for reports of BSA-catalysis of medium-sensitive reactions, see: (a) Kikuchi, K.; Thorn, S. N.; Hilvert, D. J. Am. Chem. Soc. 1996, 118, 8184-8185. (b) Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. Nature 1996, 353, 60-63].
37. For reports of medium effects in 1,3-DPC reactions see [(a) Beltrame, P.; Sartirana, P.; Vintani, C. J. Chem. Soc. (B) 1971, 814. (b) Inoue, Y.; Araki, K.; Shiraishi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3079-3083. (c) Wijnen, J. W.; Steiner, R. A.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 5389-5390]. Bovine serum albumin (BSA) does not catalyze the reaction between 1 and 2 [for reports of BSA-catalysis of medium-sensitive reactions, see: (a) Kikuchi, K.; Thorn, S. N.; Hilvert, D. J. Am. Chem. Soc. 1996, 118, 8184-8185. (b) Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. Nature 1996, 353, 60-63].
38. For reports of medium effects in 1,3-DPC reactions see [(a) Beltrame, P.; Sartirana, P.; Vintani, C. J. Chem. Soc. (B) 1971, 814. (b) Inoue, Y.; Araki, K.; Shiraishi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3079-3083. (c) Wijnen, J. W.; Steiner, R. A.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 5389-5390]. Bovine serum albumin (BSA) does not catalyze the reaction between 1 and 2 [for reports of BSA-catalysis of medium-sensitive reactions, see: (a) Kikuchi, K.; Thorn, S. N.; Hilvert, D. J. Am. Chem. Soc. 1996, 118, 8184-8185. (b) Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. Nature 1996, 353, 60-63].
39. For reports of medium effects in 1,3-DPC reactions see [(a) Beltrame, P.; Sartirana, P.; Vintani, C. J. Chem. Soc. (B) 1971, 814. (b) Inoue, Y.; Araki, K.; Shiraishi, S. Bull. Chem. Soc. Jpn. 1991, 64, 3079-3083. (c) Wijnen, J. W.; Steiner, R. A.; Engberts, J. B. F. N. Tetrahedron Lett. 1995, 36, 5389-5390]. Bovine serum albumin (BSA) does not catalyze the reaction between 1 and 2 [for reports of BSA-catalysis of medium-sensitive reactions, see: (a) Kikuchi, K.; Thorn, S. N.; Hilvert, D. J. Am. Chem. Soc. 1996, 118, 8184-8185. (b) Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. Nature 1996, 353, 60-63].
40. H-bonding to the carbonyl oxygen of 2 has been implicated in the catalytic mechanism of an antibody-catalyxed Diels-Alder reaction (Heine, A.; Stura, E. A.; Yli-Kauhaluoma, J. T.; Gao, C.; Deng, Q.; Beno, B. R.; Houk, K. N.; Janda, K. D.; Wilson, I. A. Science 1998, 279, 1934-1940).