Selective stabilization of the chorismate mutase transition state by a positively charged hydrogen bond donor

Journal of the American Chemical Society

Volumn 125, Issue 11, 2003, Pages 3206-3207

  Kienhöfer, Alexander ^a   Kast, Peter ^a   Hilvert, Donald ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; CHORISMATE MUTASE; ENZYME VARIANT;

AMINO ACID SUBSTITUTION; ARTICLE; BIOSYNTHESIS; CATALYST; CONFORMATIONAL TRANSITION; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME STABILITY; ENZYME SYNTHESIS; ESCHERICHIA COLI; HYDROGEN BOND; LIGAND BINDING; MASS SPECTROMETRY; MUTATION; NONHUMAN;

ALANINE; AMINO ACID SUBSTITUTION; ARGININE; BACILLUS SUBTILIS; CATIONS; CHORISMATE MUTASE; CITRULLINE; ENZYME STABILITY; ESCHERICHIA COLI; HYDROGEN BONDING; KINETICS; MUTAGENESIS, SITE-DIRECTED; PROTEIN CONFORMATION; RECOMBINANT FUSION PROTEINS;

EID: 0142052240     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0341992     Document Type: Article

References (30)

1. Haslam, E. Shikimic Acid: Metabolism and Metabolites; John Wiley & Sons: New York, 1993.
2. Copley, S. D.; Knowles, J. R. J. Am. Chem. Soc. 1985, 107, 5306-5308. Sogo, S. G.; Widlanski, T. S.; Hoare, J. H.: Grimshaw, C. E.; Berchtold, G. A.; Knowles, J. R. J. Am. Chem. Soc. 1984, 106, 2701-2703.
3. Copley, S. D.; Knowles, J. R. J. Am. Chem. Soc. 1985, 107, 5306-5308. Sogo, S. G.; Widlanski, T. S.; Hoare, J. H.: Grimshaw, C. E.; Berchtold, G. A.; Knowles, J. R. J. Am. Chem. Soc. 1984, 106, 2701-2703.
4. Addadi, L.; Jaffe, E. K.; Knowles, J. R. Biochemistry 1983, 22, 4494-4501. Gustin, D. J.; Mattei, P.; Kast, P.; Wiest, O.; Lee, L.; Cleland, W. W.; Hilvert, D. J. Am. Chem. Soc. 1999, 121, 1756-1757. Wiest, O.; Houk, K. N. J. Org. Chem. 1994, 59, 7582-7584.
5. Addadi, L.; Jaffe, E. K.; Knowles, J. R. Biochemistry 1983, 22, 4494-4501. Gustin, D. J.; Mattei, P.; Kast, P.; Wiest, O.; Lee, L.; Cleland, W. W.; Hilvert, D. J. Am. Chem. Soc. 1999, 121, 1756-1757. Wiest, O.; Houk, K. N. J. Org. Chem. 1994, 59, 7582-7584.
6. Addadi, L.; Jaffe, E. K.; Knowles, J. R. Biochemistry 1983, 22, 4494-4501. Gustin, D. J.; Mattei, P.; Kast, P.; Wiest, O.; Lee, L.; Cleland, W. W.; Hilvert, D. J. Am. Chem. Soc. 1999, 121, 1756-1757. Wiest, O.; Houk, K. N. J. Org. Chem. 1994, 59, 7582-7584.
7. Chook, Y. M.; Ke, H.; Lipscomb, W. N. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8600-8603. Chook, Y. M.; Gray, J. V.; Ke, H.; Lipscomb, W. N. J. Mol. Biol, 1994, 240, 476-500.
8. Chook, Y. M.; Ke, H.; Lipscomb, W. N. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8600-8603. Chook, Y. M.; Gray, J. V.; Ke, H.; Lipscomb, W. N. J. Mol. Biol, 1994, 240, 476-500.
9. Cload, S. T.; Liu, D. R.; Pastor, R. M.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 1787-1788. Kast, P.; Asif-Ullah, M.; Jiang, N.; Hilvert, D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 5043-5048.
10. Cload, S. T.; Liu, D. R.; Pastor, R. M.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 1787-1788. Kast, P.; Asif-Ullah, M.; Jiang, N.; Hilvert, D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 5043-5048.
11. Kast, P.; Grisostomi, C.; Chen, I. A.; Li, S.; Krengel, U.; Xue, Y.; Hilvert, D. J. Biol. Chem. 2000, 47, 36832-36838.
12. Lee, A. Y.; Karplus, P. A.; Ganem, B.; Clardy, J. J. Am. Chem. Soc. 1995, 117, 3627-3628.
13. Liu, D. R.; Cload, S. T.; Pastor, R. M.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 1789-1790. Zhang, S.; Kongsaeree, P.; Clardy, J.; Wilson, D. B.; Ganem, B. Bioorg. Med. Chem. 1996, 4, 1015-1020.
14. Liu, D. R.; Cload, S. T.; Pastor, R. M.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 1789-1790. Zhang, S.; Kongsaeree, P.; Clardy, J.; Wilson, D. B.; Ganem, B. Bioorg. Med. Chem. 1996, 4, 1015-1020.
15. Sträter, N.; Schnappauf, G.; Braus, G.; Lipscomb, W. N. Structure 1997, 5, 1437-1452.
16. Lyne, P. D.; Mulholland, A. J.; Richards, W. G. J. Am. Chem. Soc. 1995, 117, 11345-11350.
17. Worthington, S. E.; Roitberg, A. E.; Krauss, M. J. Phys. Chem. B 2001, 105, 7087-7095.
18. Hur, S.; Bruice, T. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 1176-1181.
19. Khanjin, N. A.; Snyder, J. P.; Menger, F. M. J. Am. Chem. Soc. 1999, 121, 11831-11846.
20. Dawson, P. E.; Kent, S. B. H. Annu. Rev. Biochem. 2000, 69, 923-960.
21. Evans, T. C.; Benner, J.; Xu, M.-Q. Protein Sci. 1998, 7, 2256-2264.
22. MacBeath, G.; Kast, P.; Hilvert, D. Biochemistry 1998, 37, 10062-10073.
23. Bartlett, P. A.; Nakagawa, Y.; Johnson, C. R.; Reich, S. H.; Luis, A. J. Org. Chem. 1988, 53, 3195-3210.
24. Gray, J. V.; Golinelli-Pimpaneau, B.; Knowles, J. R. Biochemistry 1990, 29, 376-383.
25. Mattei, P.; Kast, P.; Hilvert, D. Eur. J. Biochem. 1999, 261, 25-32.
26. See, for example: Phillips, M. A.; Fletterick, R.; Rutter, W. J. J. Biol. Chem. 1990, 265, 20692-20698. Tissot, A. C.; Vuilleumier, S.; Fersht, A. R. Biochemistry 1996, 35, 6786-6794.
27. See, for example: Phillips, M. A.; Fletterick, R.; Rutter, W. J. J. Biol. Chem. 1990, 265, 20692-20698. Tissot, A. C.; Vuilleumier, S.; Fersht, A. R. Biochemistry 1996, 35, 6786-6794.
28. Aemissegger, A.; Jaun, B.; Hilvert, D. J. Org. Chem. 2002, 67, 6725-6730.
29. Haynes, M. R.; Stura, E. A.; Hilvert, D.; Wilson, I. A. Science 1994, 263, 646-652. Hilvert, D.; Carpenter, S. H.; Nared, K. D.; Auditor, M.-T. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4953-4955.
30. Haynes, M. R.; Stura, E. A.; Hilvert, D.; Wilson, I. A. Science 1994, 263, 646-652. Hilvert, D.; Carpenter, S. H.; Nared, K. D.; Auditor, M.-T. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4953-4955.