Fatty acid amide hydrolase competitively degrades bioactive amides and esters through a nonconventional catalytic mechanism

Biochemistry

Volumn 38, Issue 43, 1999, Pages 14125-14130

  Patricelli, Matthew P ^a   Cravatt, Benjamin F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; AMIDASE; AMIDE; AMINO ACID; ESTER; ESTERASE; FATTY ACID DERIVATIVE; GLUTAMIC ACID; HYDROLASE; LYSINE; MUTANT PROTEIN; OLEIC ACID;

AMINO ACID SUBSTITUTION; ARTICLE; CATALYSIS; CONTROLLED STUDY; ENZYME DEGRADATION; PH; PRIORITY JOURNAL;

ACYLATION; AMIDES; AMIDOHYDROLASES; AMINO ACID SUBSTITUTION; ANIMALS; BINDING, COMPETITIVE; CATALYSIS; ENZYME ACTIVATION; ESTERS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; KINETICS; OLEIC ACIDS; POINT MUTATION; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0033607236     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi991876p     Document Type: Article

References (33)

1. Cravatt B. F., Giang, D. K., Mayfield, S. P., Boger, D. L., Lerner, R. A., and Gilula, N. B. (1996) Nature 384, 83-87.
2. Giang, D. K., and Cravatt, B. F. (1997) Proc. Natl. Acad. Sci. U.S.A. 94, 2238-2242.
3. Devane, W. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R. (1992) Science 258, 1946-1949.
4. Cravatt, B. F., Prospero-Garcia, O., Siuzdak, G., Gilula, N. B., Henriksen, S. J., Boger, D. L., and Lerner, R. A. (1995) Science 268, 1506-1509.
5. Lerner, R. A., Siuzdak, G., Prospero-Garcia, O., Henriksen, S. J., Boger, D. L., and Cravatt, B. F. (1994) Proc. Natl. Acad. Sci. U.S.A. 91, 9505-9508.
6. Basile, A. S., Hanus, L., and Mendelson, W. B. (1999) Neuroreport 10, 947-951.
7. Smith, P. B., Compton, D. R., Welch, S. P., Razdan, R. K., Mechoulam, R., and Martin B. R. (1994) J. Pharmacol. Exp. Ther. 270, 219-227.
8. Calignano, A., La Rana, G., Giuffrida, A., and Piomelli, D. (1998) Nature 394, 277-281.
9. Jaggar, S. L. Hasnie, F. S., Sellaturay, S., and Rice, A. S. (1998) Pain 76, 189-199.
10. Di Marzo, V., and Deutsch, D. G. (1998) Neurobiol. Dis. 5, 386-404.
11. Piomelli, D., Beltramo, M., Giuffrida, A., and Stella, N. (1998) Neurobiol. Dis. 5, 462-473.
12. Boger, D. L., Henriksen, S. J., and Cravatt, B. F. (1998) Curr. Pharm. Des. 4, 303-314.
13. Chebrou, H., Bigey, F., Arnaud, A., and Galzy, P. (1996) Biochim. Biophys. Acta 1298, 285-293.
14. Mayaux, J. F., Cerebelaud, E., Soubrier, F., Faucher, D., and Petre, D. (1990) J. Bacteriol. 172, 6764-6773.
15. Patricelli, M. P., Lovato, M. A., and Cravatt B. F. (1999) Biochemistry 38, 9804-9812.
16. Patricelli, M. P., Lashuel, H. A., Giang, D. K., Kelly, J. W., and Cravatt, B. F. (1998) Biochemistry 37, 15177-15187.
17. Gutfreund, H., and Sturtevant, J. M. (1956) Biochem. J. 63, 656-661.
18. Walsh, C. (1979) Enzymatic Reactions Mechanisms, W. H. Freeman and Co., New York.
19. Corey, D. R., and Craik, C. S. (1992) J. Am. Chem. Soc. 114, 1784-1790.
20. Bender, M. L., Schonbaum, G. R., and Zerner, B. (1962) J. Am. Chem. Soc. 84, 2540-2550.
21. Brandt, K. G., Himoe, A., and Hess, G. P. (1967) J. Biol. Chem. 242, 3973-3982.
22. Carter, P., Abrahmsen, L., and Wells, J. A. (1991) Biochemistry 30, 6142-6154.
23. Carter, P., and Wells, J. A. (1987) Science 237, 394-399.
24. Carter, P., and Wells, J. A. (1987) Nature 332, 564-568.
25. Craik, C. S., Roczniak, S., Largman, C., and Rutter, W. J. (1987) Science 237, 909-911.
26. Fersht, A. R. (1971) J. Am. Chem. Soc. 93, 3505-3515.
27. Komiyama, M., and Bender, M. L. (1979) Proc. Natl. Acad. Sci. U.S.A. 76, 557-560.
28. Sugiura, T., Kondo, S., Sukagawa, A., Nakane, S., Shinoda, A., Itoh, K., Yamashita, A., and Waku, K. (1995) Biochem. Biophys. Res. Commun. 215, 89-97.
29. Mechoulam, R., et al. (1995) Biochem. Pharmacol. 50, 83.
30. Goparaju, S. K., Ueda, N., Yamaguchi, H., and Yamamoto, S. (1998) FEBS Lett. 422, 69-73.
31. Stella, N., Schweitzer, P., and Piomelli, D. (1997) Nature 388, 773-778.
32. Kondo, S., Kondo, H., Nakane, S., Kodaka, T., Tokumura, A., Waku, K., and Sugiura, T. (1998) FEBS Lett. 429, 152-156.
33. Bisogno, T., Berrendero, F., Ambrosino, G., Cebeira, M., Ramos, J. A., Fernandez-Ruiz, J. J., and Di Marzo, V. (1999) Biochem. Biophys. Res. Commun. 256, 377-380.