Chemical and mutagenic investigations of fatty acid amide hydrolase: Evidence for a family of serine hydrolases with distinct catalytic properties

Biochemistry

Volumn 38, Issue 31, 1999, Pages 9804-9812

  Patricelli, Matthew P ^a   Lovato, Martha A ^a   Cravatt, Benjamin F ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; FATTY ACID; HYDROLASE; SERINE DEHYDRATASE;

AFFINITY LABELING; ARTICLE; CATALYSIS; CHEMICAL MUTAGENESIS; ENZYME ACTIVE SITE; ENZYME ANALYSIS; ENZYME MECHANISM; ENZYME STRUCTURE; HYDROGEN BOND; PH; PRIORITY JOURNAL; PROTEIN FAMILY; PROTON TRANSPORT;

FELIS CATUS; MAMMALIA;

EID: 0033520099     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi990637z     Document Type: Article

References (63)

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. Chebrou, H., Bigey, F., Arnaud, A., and Galzy, P. (1996) Biochim. Biophys. Acta 1298, 285-293.
3. Mayaux, J.-F., Cerbelaud, E., Soubrier, F., Faucher, D., and Petre, D. (1990) J. Bacteriol. 172, 6764-6773.
4. Kobayashi, M., Komeda, H., Nagasawa, T., Nishiyama, M., Horinouchi, S., Beppu, T., Yamada, H., and Shimizu, S. (1993) Eur. J. Biochem. 217, 327-36.
5. Hashimoto, Y., Nishiyama, M., Ikehata, O., Horinouchi, S., and Beppu, T. (1991) Biochim. Biophys. Acta 1088, 225-233.
6. Tsuchiya, K., Fukuyama, S., Kanzaki, N., Kanagawa, K., Negoro, S., and Okada, H. (1989) J. Bacteriol. 171, 3187-3191.
7. Klee, H., Montoya, A., Horodyski, F., Lichtenstein, C., Garfinkel, D., Fuller, S., Flores, C., Peschon, J., Nester, E., and Gordon, M. (1984) Proc. Natl. Acad. Sci. U.S.A. 81, 1728-1732.
8. Curnow, A. W., Hong, W., Yuan, R., Kim, S.-I., Martins, O., Winkler, W., Henkin, T. M., and Soil, D. (1997) Proc. Natl. Acad. Sci. U.S.A. 94, 11819-11826.
9. Boshoff, H. I. M., and Mizrahi, V. (1998) J. Bacteriol. 180, 5809-5814.
10. Corrick, C. M., Twomey, A. P., and Hynes, M. J. (1987) Gene 53, 63.
11. Gomi, K., Kitamoto, K., and Kumagai, C. (1991) Gene 108, 91-98.
12. Genbauffe, F. S., and Cooper, T. G. (1991) DNA Sequence 2, 19-32.
13. Ettinger, R. A., and DeLuca, H. F. (1995) Arch. Biochem. Biophys. 316, 14-19.
14. 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.
15. 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.
16. Facci, L., Dal Toso, R., Romanello, S., Buriani, A., Skaper, S. D., and Leon, A. (1995) Proc. Natl. Acad. Sci. U.S.A. 92, 3376-3380.
17. Wakamatsu, K., Masaki, T., Itoh, F., Koichi, K., and Sudo, K. (1990) Biochem. Biophys. Res. Commun. 168, 423-429.
18. Barg, J., Fride, E., Hanus, L., Levy, R., Matus-Leibovitch, N., Heldman, E., Bayewitch, M., Mechoulam, R., and Vogel, Z. (1995) Eur. J. Pharmacol. 287, 145-152.
19. 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.
20. 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.
21. Cravatt, B. F., Lerner, R. A., and Boger, D. L. (1996) J. Am. Chem. Soc. 118, 580-590.
22. Hiudobro-Toro, J., and Harris, R. A. (1996) Proc. Natl. Acad. Sci. U.S.A. 93, 8078-8082.
23. Thomas, E. A., Carson, M. J., Neal, M. J., and Sutcliffe, J. G. (1997) Proc. Natl. Acad. Sci. USA 94, 14115-14119.
24. Boger, D. L., Patterson, J. E., and Jin, Q (1998) Proc. Natl. Acad. Sci. U.SA. 95, 4102-4107.
25. Yost, C. S., Hampson, A. J., Leonoudakis, D., Koblin, D. D., Bornheim, L. M., and Gray, A. T. (1998) Anasth. Analg. 86, 1294-1300.
26. Lees, G., Edwards, M. D., Hassoni, A. A., Ganellin, C. R., and Galanakis, D. (1998) Br. J. Pharmacol. 124, 873-882.
27. Venance, L., Piomelli, D., Glowinski, J., and Giaume, C. (1995) Nature 376, 590-594.
28. Guan, X., Cravatt, B. F., Ehring, G. R., Hall, J. E., Boger, D. L., Lerner, R. A., and Gilula, N. B. (1997) J. Cell Biol. 139, 1785-1792.
29. Boger, D. L., Patterson, J. E., Guan, X., Cravatt, B. F., Lerner, R. A., and Gilula, N. B. (1998) Proc. Natl. Acad. Sci. U.S.A. 95, 4810-4815.
30. Di Marzo, V., Fontana, A., Cadas, H., Schinelli, S., Cimino, G., Schwartz, J.-C., and Piomelli, D. (1994) Nature 372, 686-691.
31. Arafat, E. S., Trimble, J. W., Andersen, R. A., Dass, C., and Desiderio, D. M. (1989) Life Sci. 45, 1679-1687.
32. Calignano, A., La Rana, G., Giuffrida, A., and Piomelli, D. (1998) Nature 394, 277-281.
33. Thomas, E. A., Cravatt, B. P., Danielson, P. E., Gilula, N. B., and Sutcliffe, J. G. (1997) J. Neurosci. Res. 50, 1047-1052.
34. Egertova, M., Giang, D. K., Cravatt, B. F., and Elphick, M. R. (1998) Proc. R. Soc. London, Ser. B: Biol. Sci. 265, 2081-2085.
35. Romero, J., Garcia-Palomero, E., Lin, S. Y., Ramos, J. A., Makriyannis, A., and Fernandez-Ruiz, J. J. (1996) Life Sci. 58, 1249-1257.
36. Koutek, B., Prestwich, G. D., Howlett, A. C., Chin, S. A., Salehani, D., Akhavan, N., and Deutsch, D. J. (1994) J. Biol. Chem. 269, 22937-22940.
37. Patterson, J. E., Ollman, I. R., Cravatt, B. F., Boger, D. L., Wong, C. H., and Lerner, R. A. (1996) J. Am. Chem. Soc. 118, 5938-5945.
38. Deutsch, D. G., Omeir, R., Arreaza, G., Salehani, D., Prestwich, G. D., Huang, Z., and Howlett, A. (1997) Biochem. Pharmacol. 53, 255-260.
39. Ackerman, E. J., Conde-Frieboes, K., and Dennis, E. A. (1995) J. Biol. Chem. 270, 445-450.
40. Huang, Z., Fayette, P., Abdullah, K., Cromlish, W. A., and Kennedy, B. P. (1996) Biochemistry 35, 3712-3721.
41. Patricelli, M. P., Lashuel, H. A., Giang, D. K., Kelly, J. W., and Cravatt B. F. (1998) Biochemistry 37, 15177-15187.
42. Brenner, S. (1988) Nature 334, 528.
43. Kobayashi, M., Fujiwara, Y., Goda, M., Komeda, H., and Shimizu, S. (1997) Proc. Natl. Acad. Sci. U.S.A. 94, 11986-11991.
44. Williams, K., LoPresti, M., and Stone, K (1997) in Techniques in Protein Chemistry VIII (Marshak, D. R., Ed.) pp 79-90, Academic Press, New York.
45. Fersht, A. R. (1985) in Enzyme Structure and Mechanism, p 156, W. H. Freeman, New York.
46. Dixon, G., Go, S., and Neurath, H. (1956) Biochim. Biophys. Acta 19, 193.
47. Brzozowski, A. M., Derewenda, U., Derewenda, Z. S., Dodson, G. G., Lawson, D. M., Turkenburg, J. P., Bjorkling, F., Huge-Jensen, B., Patkar, S. A., and Thim, L. (1991) Nature 351, 491-494.
48. Jansz, H. S., Posthumus, C. H., and Cohen, J. A. (1959) Biochim. Biophys. Acta 33, 396-403.
49. Augusteyn, R. C., de Jersey, J., Webb, E. C., and Zerner, B. (1969) Biochim. Biophys. Acta 171, 128-137.
50. Bachovchin, W. W., Kaiser, R., Richards, J. H., and Roberts, J. D. (1981) Proc. Natl. Acad. Sci. U.S.A. 78, 7323-7326.
51. Giang, D. K., and Cravatt, B. F. (1997) Proc. Natl. Acad. Sci. U.S.A. 94, 2238-2242.
52. Paetzel, M., Dalbey, R. E., and Strynadka, N. C. J. (1998) Nature 396, 186-190.
53. Maylie, M. F., Charles, M., and Desnuelle, P. (1972) Biochim. Biophys. Acta 276, 162-175.
54. Nicolas, A., Egmond, M., Verrips, C. T., Vlieg, J., Longhi, S., Cambillau, C., and Martinez, C. (1996) Biochemistry 35, 398-410.
55. Strynadka, N. C. J., Adachi, H., Jensen, S. E., Johns, K., Sielecki, A., Betzel, C., Sutoh, K., and James, M. N. G. (1992) Nature 359, 700-705.
56. Maveyraud, L., Pratt, R. F., and Samama, J.-P. (1998) Biochemistry 37, 2622-2628.
57. Palm, G. J., Lubkowski, J., Derst, C., Schleper, S., Rohm, K.-H., and Wlodawer, A. (1996) FEBS Lett. 390, 211-216.
58. Bryan, P., Pantoliano, M. W., Quill, S. G., Hsiao, H.-Y., and Poulos, T. (1986) Proc. Natl. Acad. Sci. U.S.A. 83, 3743-3745.
59. Jacob, F., Joris, B., Lepage, S., Dusart, J., and Frere, J. M. (1990) Biochem. J. 271, 399-406.
60. Carter, P., and Wells, J. A. (1988) Nature 332, 564-568.
61. Dodson, G., and Wlodawer, A. (1998) Trends Biochem. Sci. 23, 347-352.
62. Lin, L. L., and Little, J. W. (1989) J. Mol. Biol. 210, 439-452.
63. Okada, H., Negoro, S., Kimura, H., and Nakamura, S. (1983) Nature 306, 203-206.