Low barrier hydrogen bond is absent in the catalytic triads in the ground state but is present in a transition-state complex in the prolyl oligopeptidase family of serine proteases

Journal of Biological Chemistry

Volumn 272, Issue 41, 1997, Pages 25547-25554

  Kahyaoglu, Ara ^a   Haghjoo, Khadijeh ^a   Guo, Fusheng ^a   Jordan, Frank ^a   Kettner, Charles ^b   Felföldi, Ferenc ^c   Polgár, László ^c  

^a RUTGERS UNIVERSITY   (United States)

^b DUPONT COMPANY   (United States)

^c INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID; BORONIC ACID DERIVATIVE; HISTIDINE; HYDROGEN; LEUCINE; PROLYL ENDOPEPTIDASE; SERINE PROTEINASE; SUBTILISIN; VALINE;

ARTICLE; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITION; ENZYME KINETICS; ENZYME SUBSTRATE COMPLEX; HYDROGEN BOND; PHASE TRANSITION; PRIORITY JOURNAL; PROTEIN FAMILY; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; ANTIPAIN; CATALYSIS; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; PROTEASE INHIBITORS; PROTEIN CONFORMATION; SERINE ENDOPEPTIDASES; SWINE;

EID: 0030868993     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.272.41.25547     Document Type: Article

References (36)

1. Frey, P. A., Whitt, S. A., and Tobin, J. B. (1994) Science 264, 1927-1930
2. Frey, P. A. (1995) Science 269, 104-106
3. Tobin, J. B., Whitt, S. A., Cassidy, C. S., and Frey, P. A. (1995) Biochemistry 34, 6919-6924
4. Kreevoy, M. M., and Cleland, W. W. (1994) Science 264, 1887-1890
5. Cleland, W. W., and Kreevoy, M. M. (1995) Science 269, 104
6. Warshel, A., Papazyan, A., and Kollman, P. A. (1995) Science 269, 102-104
7. Hibbert, F., and Emsley, J. (1990) Adv. Phys. Org. Chem. 26, 255-379
8. Robillard, G., and Schulman, R. G. (1972) J. Mol. Biol. 71, 507-511
9. Robillard, G., and Schulman, R. G. (1974) J. Mol. Biol. 74, 519-540
10. Robillard, G., and Schulman, R. G. (1974). J. Mol. Biol. 74, 541-548
11. Markley, J. L. (1978) Biochemistry 17, 4648-4656
12. Markley, J. L., and Westler, W. W. (1996) Biochemistry 35, 11092-11097
13. Jordan, F., and Polgár, L. (1981) Biochemistry 20, 6366-6370
14. Zhong, S., Haghjoo, K., Kettner, C., and Jordan, F. (1995) J. Am. Chem. Soc. 117, 7047-7055
15. Zhong, S. (1991) Multinuclear NMR Studies of Boronic Acid Transition State Inhibitors of Serine Proteases. Ph.D. thesis, Rutgers, Newark, NJ
16. Haghjoo, K. (1996) Nuclear Magnetic Resonance Investigation of the Interaction of Serine Proteases with Protease Inhibitors. Ph.D. thesis, Rutgers, Newark, NJ
17. Bachovchin, W. W. (1985) Proc. Natl. Acad. Sci. U. S. A. 82, 7948-7951
18. Bachovchin, W. W. (1986) Biochemistry 25, 7751-7759
19. Rawlings, N. D., Polgár, L., and Barrett, A. J. (1991) Biochem. J. 279, 907-911
20. Polgár, L. (1994) Methods Enzymol. 244, 188-200
21. Tsuru, D., and Yoshimoto, T. (1994) Methods Enzymol. 244, 201-215
22. Polgár, L. (1992) FEBS Lett. 311, 281-284
23. Kanatani, A., Masuda, T., Shimoda, T., Misoka, F., Lin, X. S., Yoshimoto, T., and Tsuru, D. (1991) J. Biochem. (Tokyo) 110, 315-320
24. Strongin, A. Y., Izotova, L. S., Abramov, Z. T., Gorodetsky, D. I., Ermakova, L. M., Baratova, L. A., Belyanova, L. P., and Stepanov, V. M. (1978) J. Bacteriol. 133, 1401-1411
25. Kettner, C. A., and Shenvi, A. B. (1984) J. Biol. Chem. 259, 15106-15114
26. Wilk, S., and Orlowski, M. (1983) J. Neurochem. 41, 69-75
27. Kahyaoglu, A., Haghjoo, K., Kraicsovits, F., Jordan, F., and Polgár, L. (1997) Biochem. J. 322, 839-843
28. Bachovchin, W. W., Wong, W. Y. L., Farr-Jones, S., Shenvi, A. B., and Kettner, C. A. (1988) Biochemistry 27, 7689-7697
29. Liang, T.-C., and Abeles, R. H. (1987) Biochemistry 26, 7603-7608
30. Halkides, C. J., Wu, Y. Q., and Murray, C. J. (1996) Biochemistry 35, 15941-15948
31. Adebodun, F., and Jordan, F. (1989) J. Cell. Biochem. 40, 249-260
32. Kintanar, A., Metzler, C. M., Metzler, D. E., and Scott, R. D. (1991) J. Biol. Chem. 266, 17222-17229
33. Metzler, D. E., Metzler, C. M., Mollova, E. T., Scott, R. D., Tanase, S., Kogo, K., Higaki, T., and Morino, Y. (1994) J. Biol. Chem. 269, 28017-28026
34. Metzler, D. E., Metzler, C. M., Scott, R. D., Mollova, E. T., Kagamiyama, H., Yano, T., Kuramitsu, S., Hayashi, H., Hirotsu, K., and Miyahara, I. (1994) J. Biol. Chem. 269, 28027-28033
35. Tong, H., and Davis, L. (1995) Biochemistry 34, 3362-3367
36. Hore, P. J. (1983) J. Magn. Reson. 55, 283-300