The tautomeric half-reaction of BphD, a C-C bond hydrolase: Kinetic and structural evidence supporting a key role for histidine 265 of the catalytic triad

Journal of Biological Chemistry

Volumn 282, Issue 27, 2007, Pages 19894-19904

  Horsman, Geoff P ^a   Bhowmik, Shiva ^b   Seah, Stephen Y K ^a   Kumar, Pravindra ^b   Bolin, Jeffrey T ^b   Eltis, Lindsay D ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b Purdue University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BPHD-CATALYZED HYDROLYSIS; ENOL-KETO TAUTOMERIZATION; TAUTOMERIC HALF-REACTION;

CATALYST ACTIVITY; CHEMICAL BONDS; HYDROLYSIS; MOLECULAR INTERACTIONS; REACTION KINETICS;

ENZYME KINETICS;

2 HYDROXY 6 OXO 6 PHENYLHEXA 2,4 DIENOIC ACID; ALKADIENE; HISTIDINE; HYDROLASE; PROTEIN BPHD; SERINE DEHYDRATASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; ENZYME STRUCTURE; MOLECULAR DYNAMICS; PRIORITY JOURNAL; PROTEIN FUNCTION; STRUCTURE ANALYSIS; TAUTOMERIC SHIFT; WILD TYPE;

BACTERIAL PROTEINS; BURKHOLDERIA; CATALYSIS; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; FATTY ACIDS, UNSATURATED; HISTIDINE; HYDROLASES; HYDROLYSIS; KINETICS; MODELS, MOLECULAR; PROTEIN STRUCTURE, QUATERNARY;

BURKHOLDERIA XENOVORANS;

EID: 34547094599     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M702237200     Document Type: Article

References (39)

1. Vaillancourt, F. H., Bolin, J. T., and Eltis, L. D. (2006) Crit. Rev. Biochem. Mol. Biol. 41, 241-267
2. Seah, S. Y. K., Labbé, G., Nerdinger, S., Johnson, M. R., Snieckus, V., and Eltis, L. D. (2000) J. Biol. Chem. 275, 15701-15708
3. Furukawa, K. (2003) Trends Biotechnol. 21, 187-190
4. Van der Geize, R., Yam, K., Heuser, T., Wilbrink, M. H., Hara, H., Anderton, M. C., Sim, E., Dijkhuizen, L., Davies, J. E., Mohn, W. W., and Eltis, L. D. (2007) Proc. Natl. Acad. Sci. U. S. A. 104, 1947-1952
5. Rengarajan, J., Bloom, B. R., and Rubin, E. J. (2005) Proc. Natl. Acad. Sci. U. S. A. 102, 8327-8332
6. Bugg, T. D. H. (2004) Bioorg. Chem. 32, 367-375
7. Heikinheimo, P., Goldman, A., Jeffries, C., and Ollis, D. L. (1999) Structure 7, 141-146
8. Holmquist, M. (2000) Curr. Prot. Pept. Sci. 1, 209-235
9. Ollis, D. L., Cheah, E., Cygler, M., Dijkstra, B., Frolow, F., Franken, S. M., Harel, M., Remington, S. J., Silman, I., Schrag, J., Sussman, J. L., Verscheuren, K. H. G., and Goldman, A. (1992) Protein Eng. 5, 197-211
10. Henderson, I. M. J., and Bugg, T. D. H. (1997) Biochemistry 36, 12252-12258
11. Lam, W. W. Y., and Bugg, T. D. H. (1997) Biochemistry 36, 12242-12251
12. Fleming, S. M., Robertson, T. A., Langley, G. J., and Bugg, T. D. H. (2000) Biochemistry 39, 1522-1531
13. Li, J. J., Li, C., Blindauer, C. A., and Bugg, T. D. H. (2006) Biochemistry 45, 12461-12469
14. Speare, D. M., Fleming, S. M., Beckett, M. N., Li, J. J., and Bugg, T. D. H. (2004) Org. Biomol. Chem. 2, 2942-2950
15. Speare, D. M., Olf, P., and Bugg, T. D. H. (2002) Chem. Commun., 2304-2305
16. Li, J. J., and Bugg, T. D. H. (2007) Org. Biomol. Chem. 5, 507-513
17. Dunn, G., Montgomery, M. G., Mohammed, F., Coker, A., Cooper, J. B., Robertson, T., Garcia, J. L., Bugg, T. D. H., and Wood, S. P. (2005) J. Mol. Biol. 346, 253-265
18. Li, C., Montgomery, M. G., Mohammed, F., Li, J. J., Wood, S. P., and Bugg, T. D. H. (2005) J. Mol. Biol. 346, 241-251
19. Horsman, G. P., Ke, J., Dai, S., Seah, S. Y. K., Bolin, J. T., and Eltis, L. D. (2006) Biochemistry 45, 11071-11086
20. D'Ordine, R. L., Tonge, P. J., Carey, P. R., and Anderson, V. E. (1994) Biochemistry 33, 12635-12643
21. Tian, F., Debler, E. W., Millar, D. P., Deniz, A. A., Wilson, I. A., and Schultz, P. G. (2006) Angew. Chem. Int. Ed. Engl. 45, 7763-7765
22. Sekharan, S., Sugihara, M., and Buss, V. (2007) Angew. Chem., Int. Ed. Engl. 46, 269-271
23. Nerdinger, S., Kendall, C., Marchhart, R., Riebel, P., Johnson, M. R., Yin, C. F., Eltis, L. D., and Snieckus, V. (1999) Chem. Commun., 2259-2260
24. Seah, S. Y. K., Terracina, G., Bolin, J. T., Riebel, P., Snieckus, V., and Eltis, L. D. (1998) J. Biol. Chem. 273, 22943-22949
25. Otwinowski, Z., and Minor, W. (1997) Methods Enzymol. 276, 307-326
26. Bailey, S. (1994) Acta Crystallogr., Sect. D: Biol. Crystallogr. 50, 760-763
27. Vagin, A., and Teplyakov, A. (1997) J. Appl. Crystallogr. 30, 1022-1025
28. Murshudov, G. N., Vagin, A. A., and Dodson, E. J. (1997) Acta Crystallogr., Sect. D: Biol. Crystallogr. 53, 240-255
29. Jones, T. A., Zou, J. Y., Cowan, S. W., and Kjeldgaard, M. (1991) Acta Crystallogr. Sect. A 47, 110-119
30. Schuttelkopf, A. W., and van Aalten, D. M. F. (2004) Acta Crystallogr. Sect. D: Biol. Crystallogr. 60, 1355-1363
31. Laskowski, R., MacArthur, M., Moss, D., and Thornton, J. (1993) J. Appl. Crystallogr. 26, 283-291
32. Word, J. M., Lovell, S. C., Richardson, J. S., and Richardson, D. C. (1999) J. Mol. Biol. 285, 1735-1747
33. Nandhagopal, N., Yamada, A., Hatta, T., Masai, E., Fukuda, M., Mitsui, Y., and Senda, T. (2001) J. Mol. Biol. 309, 1139-1151
34. Williams, D. H., and Fleming, I. (1995) Spectroscopic Methods in Organic Chemistry, 5th Ed., pp. 14-17, McGraw-Hill, London
35. Takahashi, Y., and Ebrey, T. G. (2003) Biochemistry 42, 6025-6034
36. Li, J. J., and Bugg, T. D. H. (2005) Chem. Commun., 130-132
37. Fox, M. A., and Whitesell, J. K. (1994) Organic Chemistry, p. 204, Jones and Bartlett Publishers, Inc., London
38. Diaz, E., and Timmis, K. N. (1995) J. Biol. Chem. 270, 6403-6411
39. Fushinobu, S., Saku, T., Hidaka, M., Jun, S. Y., Nojiri, H., Yamane, H., Shoun, H., Omori, T., and Wakagi, T. (2002) Protein Sci. 11, 2184-2195