Relaxing substrate specificity in antibody-catalyzed reactions: Enantioselective hydrolysis of N-Cbz-amino acid esters

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2332-2339

  Tanaka, Fujie ^a   Kinoshita, Keiko ^a   Tanimura, Ryuji ^a   Fujii, Ikuo ^a  

^a BIOMOL ENG RESEARCH INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ANTIBODY; HAPTEN;

ARTICLE; CATALYSIS; DRUG DESIGN; ENANTIOMER; ENZYME SPECIFICITY; HYDROLYSIS; REACTION ANALYSIS;

EID: 0029925034     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952220w     Document Type: Article

References (39)

1. (1) Reviews: (a) Schultz, P. G.; Lemer, R. A. Acc. Chem. Res. 1993, 26, 391-395. (b) Lemer, R. A.: Benkovic, S. J.; Schultz, P. G. Science 1991, 252, 659-667.
2. (1) Reviews: (a) Schultz, P. G.; Lemer, R. A. Acc. Chem. Res. 1993, 26, 391-395. (b) Lemer, R. A.: Benkovic, S. J.; Schultz, P. G. Science 1991, 252, 659-667.
3. Iwabuchi, Y.; Miyashita, H.; Tanimura, R.; Kinoshita, K.; Kikuchi, M.; Fujii, I. J. Am. Chem. Soc. 1994, 116, 771-772.
4. (a) Li, T.; Hilton, S.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 2123-2127.
5. (b) Hsieh, L. C.: Yonkovich, S.; Kochersperger, L.; Schultz, P. G. Science 1993, 260, 337-339.
6. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
7. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
8. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
9. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
10. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
11. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
12. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
13. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
14. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
15. For some recent examples of preparing chiral α-amino acid derivatives, see references in: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848. (b) Lander, P. A.; Hegedus, L. S. J. Am. Chem. Soc. 1994, 116, 8126-8132. (c) Guo, J.; Huang, W.; Scanlan, T. S. J. Am. Chem. Soc. 1994, 116, 6062-6069. (d) RajanBabu, T. V.; Avers. T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4104-4102. (e) Mulzer, J.: Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew: Chem., Int. Ed. Engl. 1994, 33, 1737-1739. (f) Kazmair, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999. (g) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Halow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (h) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030. (i) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810. (J) Vejejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612-11613.
16. For some examples of the enzymatic kinetic resolution of amino acid derivatives, see references in: (a) Chenault, H. K.; Dahmer, J.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 6354-6364. (b) Miyazawa, T.; Iwanaga, H.: Ueji, S.; Yamada, T.; Kuwata, S. Chem. Lett. 1989, 2219-2222. (c) Chen, S.-T.; Wang, K.-T.; Wong, C.-H. J. Chem. Soc., Chem. Commun. 1986, 1514-1516.
17. For some examples of the enzymatic kinetic resolution of amino acid derivatives, see references in: (a) Chenault, H. K.; Dahmer, J.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 6354-6364. (b) Miyazawa, T.; Iwanaga, H.: Ueji, S.; Yamada, T.; Kuwata, S. Chem. Lett. 1989, 2219-2222. (c) Chen, S.-T.; Wang, K.-T.; Wong, C.-H. J. Chem. Soc., Chem. Commun. 1986, 1514-1516.
18. For some examples of the enzymatic kinetic resolution of amino acid derivatives, see references in: (a) Chenault, H. K.; Dahmer, J.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 6354-6364. (b) Miyazawa, T.; Iwanaga, H.: Ueji, S.; Yamada, T.; Kuwata, S. Chem. Lett. 1989, 2219-2222. (c) Chen, S.-T.; Wang, K.-T.; Wong, C.-H. J. Chem. Soc., Chem. Commun. 1986, 1514-1516.
19. (a) Davies, D. R.; Padlan, E. A. Annu. Rev. Biochem. 1990, 59, 439-473 and references cited therein.
20. (b) Arevalo, J. H.: Taussing, M. J.; Wilson, I. A. Nature 1993, 365, 859-863.
21. 2O showed 0.6% NOE of the Cbz phenyl proton and 9.6% NOE of the meta proton of the nitro group when the ortho proton of the nitro group was irradiated.
22. The packed conformation of phosphonate 3 was optimized by Discover CVFF, and the value was calculated using Insight II (Biosym Technologies) with a 1.7 A probe sphere and van der Waals radii.
23. Janda, K. D.; Benkovic, S. J.; Lemer, R. A. Science 1989, 244, 437-440.
24. Kohler, G.; Milstein, C. Nature 1975, 256, 495-497.
25. Miyashita, H.; Karaki, Y.; Kikuchi, M.; Fujii, I. Proc. Natl. Acad. Sci. USA . 1993, 90, 5337-5340.
26. Nishino, N.; Powers, J. C. J. Biol. Chem. 1980, 255, 3482-3486 and references cited therein.
27. 14 of the activity titrations, with phosphonate (R)-3 for antibody 7G2 or (S)-3 for antibody 3G2.
28. Henderson, P.J. F. Biochem. J. 1972, 127, 321-333.
29. Friguet, B.; Chaffotte, A. F.; Djavadi-Ohaniance, L.; Goldberg, M. E. J. Immunol. Methods 1985, 77, 305-319.
30. 18
31. For an example: Tarasow, T. M.; Lewis, C.; Hilvert, D. J. Am. Chem. Soc. 1994, 116. 7959-7963.
32. Fujii, I.; Tanaka, F.: Miyashita, H.; Tanamura, R.; Kinoshita, K. J. Am. Chem. Soc. 1995, 117, 6199-6209.
33. 6b
34. Catalytic antibodies with either A or S substrate specificity are expected to show kinetic resolution: (a) Reference 10. (b) Sinha, S. C.; Keinan, E.; Reymond, J.-L. J. Am. Chem. Soc. 1993, 115, 4893-4894. (c) Pollack, S. J.; Hsiun, P.; Schultz, P. G. J. Am. Chem. Soc. 1989, 111, 5961-5962. (d) Napper, A. D.; Benkovic, S. J.; Tramontano, A.; Lerner, R. A. Science 1987, 237, 1041-1043.
35. Catalytic antibodies with either A or S substrate specificity are expected to show kinetic resolution: (a) Reference 10. (b) Sinha, S. C.; Keinan, E.; Reymond, J.-L. J. Am. Chem. Soc. 1993, 115, 4893-4894. (c) Pollack, S. J.; Hsiun, P.; Schultz, P. G. J. Am. Chem. Soc. 1989, 111, 5961-5962. (d) Napper, A. D.; Benkovic, S. J.; Tramontano, A.; Lerner, R. A. Science 1987, 237, 1041-1043.
36. Catalytic antibodies with either A or S substrate specificity are expected to show kinetic resolution: (a) Reference 10. (b) Sinha, S. C.; Keinan, E.; Reymond, J.-L. J. Am. Chem. Soc. 1993, 115, 4893-4894. (c) Pollack, S. J.; Hsiun, P.; Schultz, P. G. J. Am. Chem. Soc. 1989, 111, 5961-5962. (d) Napper, A. D.; Benkovic, S. J.; Tramontano, A.; Lerner, R. A. Science 1987, 237, 1041-1043.
37. Catalytic antibodies with either A or S substrate specificity are expected to show kinetic resolution: (a) Reference 10. (b) Sinha, S. C.; Keinan, E.; Reymond, J.-L. J. Am. Chem. Soc. 1993, 115, 4893-4894. (c) Pollack, S. J.; Hsiun, P.; Schultz, P. G. J. Am. Chem. Soc. 1989, 111, 5961-5962. (d) Napper, A. D.; Benkovic, S. J.; Tramontano, A.; Lerner, R. A. Science 1987, 237, 1041-1043.
38. uncat) of If was lower than that of the other substrates, the velocity of the L-ester hydrolysis by antibody 7G12 was 2 orders of magnitude lower than that of the other L-esters. Although ester If, with a bulky substituent, was more resistant to hydrolysis, it was enantioselectively (9:1) hydrolyzed by antibody 7G12.
39. Hirschmann, R.; Smith, A. B., III; Taylor. C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J. Science 1994, 265, 234-237.