Structural basis for herbicidal inhibitor selectivity revealed by comparison of crystal structures of plant and mammalian 4-hydroxyphenylpyruvate dioxygenases

Biochemistry

Volumn 43, Issue 32, 2004, Pages 10414-10423

  Yang, Cheng ^a   Pflugrath, James W ^a   Camper, Debra L ^b   Foster, Mendy L ^b   Pernich, Daniel J ^b   Walsh, Terence A ^b  

^a Rigaku/MSC Inc   (United States)

^b DOW AGROSCIENCES LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; CRYSTALLIZATION; ENZYMES; HERBICIDES; PLANTS (BOTANY);

AGROCHEMICALS; PLANT SELECTIVITY;

BIOCHEMISTRY;

4 HYDROXYPHENYLPYRUVATE DIOXYGENASE; HERBICIDE;

ARABIDOPSIS; ARTICLE; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME STRUCTURE; HYDROGEN BOND; MICHAELIS CONSTANT; NONHUMAN; PRIORITY JOURNAL; RAT; STEREOCHEMISTRY;

4-HYDROXYPHENYLPYRUVATE DIOXYGENASE; AMINO ACID SEQUENCE; ANIMALS; ARABIDOPSIS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; HERBICIDES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PROTEIN CONFORMATION; PYRAZOLES; RATS; SEQUENCE HOMOLOGY, AMINO ACID; STRUCTURE-ACTIVITY RELATIONSHIP;

ARABIDOPSIS; ARABIDOPSIS THALIANA; MAMMALIA;

EID: 4043073398     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi049323o     Document Type: Article

References (31)

1. Pallett, K. E., Little, J. P., Sheekey, M., and Veerasekaran, P. (1998) The mode of action of isoxaflutole I. physiological effects, metabolism, and selectivity, Pestic. Biochem. Physiol. 62, 113-124.
2. Mitchell, G., Bartlett, D. W., Fraser, T. E. M., Hawkes, T. R., Holt, D. C., Townson, J. K., and Wiehert, R. A. (2001) Mesotrione: a new selective herbicide for use in maize, Pest Manage. Sci. 57, 120-128.
3. Cerone, R., Holme, E., Schiaffino, M. C., Caruso, U., Maritano, L., and Romano, C. (1997) Tyrosinemia type III: diagnosis and ten-year follow-up, Acta Paediatr. 86, 1013-1015.
4. Endo, F., Kitano, A., Uehara, I., Nagata, N., Matsuda, I., Shinka, T., Kuhara, T., and Matsumoto, I. (1983) Four-hydroxyphenylpyruvic acid oxidase deficiency with normal fumarylacetoacetase: a new variant form of hereditary hypertyrosinemia, Pediatr. Res. 17, 92-96.
5. Sanchez-Amat, A., Ruzafa, C., and Solano, F. (1998) Comparative tyrosine degradation in Vibrio cholerae strains. The strain ATCC 14035 as a prokaryotic melanogenic model of homogentisate-releasing cell, Comp. Biochem. Biophys. B119, 557-562.
6. Tomoeda, K., Awata, H., Matsuura, T., Matsuda, I., Ploechl, E., Milovac, T., Boneh, A., Scott, C. R., Danks, D. M., and Endo, F. (2000) Mutations in the 4-hydroxyphenylpyruvic acid dioxygenase gene are responsible for tyrosinemia type III and hawkinsinuria, Mol. Genet. Metab. 71, 506-510.
7. Holme, E., and Lindstedt, S. (1998) Tyrosinaemia type I and NTBC (2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione), J. Inherited Metab. Dis. 21, 507-517.
8. Norris, S. R., Barrette, T. R., and DellaPenna, D. (1995) Genetic dissection of carotenoid synthesis in Arabidopsis defines plastoquinone as an essential component of phytoene desaturation, Plant Cell 7, 2139-2149.
9. Ryle, M. J., and Hausinger, R. P. (2002) Non-heme iron oxygenases, Curr. Opin. Chem. Biol. 6, 193-201.
10. Crouch, N. P., Adlington, R. M., Baldwin, J. E., Lee, M. H., and Mackinnon, C. H. (1997) A mechanistic rationalization for the substrate specificity of recombinant mammalian 4-hydroxyphenylpyruvate dioxygenase (4-HPPD), Tetrahedron 53, 6993-7010.
11. Serre, L., Sailland, A., Sy, D., Boudec, P., Rolland, A., Pebay-Peyroula, E., and Cohen-Addad, C. (1999) Crystal structure of Pseudomonas fluorescens 4-hydroxyphenylpyruvate dioxygenase: an enzyme involved in the tyrosine degradation pathway, Structure 7, 977-988.
12. Fritze, I. M., Linden, L., Freigang, J., Auerbach, G., Huber, R., and Steinbacher, S. (2004) The crystal structures of Zea mays and Arabidopsis 4-hydroxyphenylpyruvate dioxygenase, Plant Physiol 134, 1388-1400.
13. Pallett, K. E., Cramp, S. M., Little, J. P., Veerasekaran, P., Crudace, A. J., and Slater, A. E. (2001) Isoxaflutole: the background to its discovery and the basis of its herbicidal properties, Pest Manage. Sci. 57, 133-142.
14. Lee, D. L., Knudsen, C. G., Michaely, W. J., Chin, H. L., Nguyen, N. H., Carter, C. G., Cromartie, T. H., Lake, B. H., Shribbs, J. M., and Fraser, T. (1998) The structure-activity relationships of the triketone class of p-hydroxyphenylpyruvate dioxygenase inhibiting herbicides, Pestic. Sci. 54, 377-384.
15. Meazza, G., Scheffler, B. E., Tellez, M. R., Rimando, A. M., Romagni, J. G., Duke, S. O., Nanayakkara, D., Khan, I. A., Abourashed, E. A., and Dayan, F. E. (2002) The inhibitory activity of natural products on plant p-hydroxyphenylpyruvate dioxygenase, Phytochemistry 60, 281-288.
16. Garcia, I., Job, D., and Matringe, M. (2000) Inhibition of p-hydroxyphenylpyruvate dioxygenase by the diketonitrile of isoxaflutole: A case of half-site reactivity, Biochemistry 39, 7501-7507.
17. Ellis, M. K., Whitfield, A. C., Gowans, L. A., Auton, T. R., Provan, W. M., Lock, E. A., Lee, D. L., and Smith, L. L. (1996) Characterization of the interaction of 2-[2-Nitro-4-(trifluoromethyl)benzoyl]-4,4,6,6- tetramethylcyclohexane-1,3,5-trione with rat hepatic 4-hydroxyphenylpyruvate dioxygenase, Chem. Res. Toxicol. 9, 24-27.
18. Kavana, M., and Moran, G. R. (2003) Interaction of (4-hydroxyphenyl) pyruvate dioxygenase with the specific inhibitor 2-[2-nitro-4-(trifluoromethyl) benzoyl]-1,3-cyclohexanedione, Biochemistry 42, 10238-10245.
19. Neidig, M. L., Kavana, M., Moran, G. R., and Solomon, E. I. (2004) CD and MCD studies of the non-heme ferrous active site in (4-hydroxyphenyl)pyruvate dioxygenase: Correlation between oxygen activation in the extradiol and α-kg-dependent dioxygenases, J. Am. Chem. Soc. 126, 4486-4487.
20. Lock, E. A., Ellis, M. K., Gaskin, P., Robinson, M., Auton, T. R., Provan, W. M., Smith, L. L., Prisbylla, M. P., Mutter, L. C., and Lee, D. L. (1998) From toxicological problem to therapeutic use: The discovery of the mode of action of 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione (NTBC), its toxicology and development as a drug, J. Inherited Metab. Dis. 21, 498-506.
21. Lee, D. L., Prisbylla, M. P., Cromartie, T. H., Dagarin, D. P., Howard, S. W., Provan, W. M., Ellis, M. K., Fraser, T., and Mutter, L. C. (1997) The discovery and structural requirements of inhibitors of p-hydroxyphenylpyruvate dioxygenase, Weed Sci. 45, 601-609.
22. Studier, F. W., Rosenberg, A. H., Dunn, J. J., and Dubendorff, J. W. (1990) Use of T7 RNA polymerase to direct expression of cloned genes, Methods Enzymol. 185, 60-89.
23. Secor, J. (1994) Inhibition of barnyardgrass 4-hydroxyphenylpyruvate dioxygenase by sulcotrione, Plant Physiol. 106, 1429-1433.
24. Schmidt, S. R., Mueller, C. R., and Kress, W. (1995) Murine liver homogentisate 1,2-dioxygenase. Purification to homogeneity and novel biochemical properties, Eur. J. Biochem. 228, 425-430.
25. Pflugrath, J. W. (1999) The finer things in X-ray diffraction data collection, Acta Crystallogr. D55, 1718-1725.
26. Bailey, S. (1994) The CCP4 suite: programs for protein crystallography, Acta Crystallogr. D50, 760-763.
27. Jones, T. A., Zhou, J. Y., Cowan, S. W., and Kjeldgaard, M. (1991) Improved methods of building protein models in electron density maps and the location errors in these methods, Acta Crystallogr. A47, 110-119.
28. Yang, C., and Pflugrath, J. W. (2001) Applications of anomalous scattering from S atoms for improved phasing of protein diffraction data collected at Cu Ka wavelength, Acta Crystallogr. D57, 1480-1490.
29. Valegard, K., Terwisscha van Scheltinga, A. C., Lloyd, M. D., Hara, T., Ramaswamy, S., Perrakis, A., Thompson, A., Lee, H. J., Baldwin, J. E., Schofield, C. J., Hajdu, J., and Andersson, I. (1998) Structure of a cephalosporin synthase, Nature 394, 805-809.
30. Zhang, Z., Ren, J., Stammers, D. K., Baldwin, J. E., Harlos, K., and Schofield, C. J. (2000) Structural origins of the selectivity of the trifunctional oxygenase clavaminic acid synthase, Nat. Struct. Biol. 7, 127-133.
31. Siddall, T. L., Ouse, D. G., Benko, Z. L., Garvin, G. M., Jackson, J. L., McQuiston, J. M., Ricks, M. J., Thibault, T. D., Turner, J. A., Vanheertum, J. C., and Weimer, M. R. (2003) Synthesis and herbicidal activity of phenyl-substituted benzoylpyrazoles, Pest Manage. Sci. 58, 1175-1186.