Kinetic and molecular analysis of 5-epiaristolochene 1,3-dihydroxylase, a cytochrome P450 enzyme catalyzing successive hydroxylations of sesquiterpenes

Journal of Biological Chemistry

Volumn 280, Issue 5, 2005, Pages 3686-3696

  Takahashi, Shunji ^a   Zhao, Yuxin ^b   O'Maille, Paul E ^c   Greenhagen, Bryan T ^a   Noel, Joseph P ^c   Coates, Robert M ^b   Chappell, Joe ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CATALYST ACTIVITY; HYDROXYLATION; KETONES; MUTAGENESIS; REACTION KINETICS;

5-EPIARISTOLOCHEME (EA); CAPSIDIOL; CYTOCHROME; HYDROSYLATION;

ENZYME KINETICS;

1 BETA HYDROXY 5 EPIARISTOLOCHENE; 5 EPIARISTOLOCHENE; CAPSIDIOL; CYTOCHROME P450; PROTEIN 5 EPIARISTOLOCHENE 1,3 DIHYDROXYLASE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BIOSYNTHESIS; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME BINDING; ENZYME KINETICS; ENZYME SPECIFICITY; HYDROXYLATION; MUTATIONAL ANALYSIS; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN FUNCTION; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY;

AMINO ACID SEQUENCE; BINDING SITES; CYTOCHROME P-450 ENZYME SYSTEM; HYDROXYLATION; ISOLEUCINE; KINETICS; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; PROTEIN STRUCTURE, TERTIARY; SERINE; SESQUITERPENES; SUBSTRATE SPECIFICITY; TOBACCO;

FELIS CATUS;

EID: 13544272051     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M411870200     Document Type: Article

References (72)

1. Stevens, K. L. (1984) Isopentenoids in Plants, pp. 63-80, Marcel Dekker, Inc., New York
2. Kessler, A., and Baldwin, I. T. (2001) Science 291, 2141-2144
3. Gibson, R. W., and Pickett, J. A. (1983) Nature 302, 608-609
4. Chappell, J. (1995) Plant Physiol. 107, 1-6
5. Stoessl, A., Stothers, J. B., and Ward, E. W. B. (1976) Phytochemistry 15, 855-873
6. Stoessl, A., Unwin, C. H., and Ward, E. W. B. (1973) Phytopathology 63, 1225-1231
7. Ward, E. W. B., Unwin, C. H., and Stoessl, A. (1973) Phytopathology 63, 1537-1538
8. Guedes, M. E. M., Kuc, J., Hammerschmidt, R., and Bostock, R. (1982) Phytochemistry 21, 2987-2988
9. Watson, D. G., Rycroft, D. S., Freer, I. M., and Brooks, C. J. W. (1985) Phytochemistry 24, 2195-2200
10. Chappell, J., Nable, R., Fleming, P., Andersen, R. A., and Burton, H. R. (1987) Phytochemistry 26, 2259-2260
11. Stoessl, A., Unwin, C. H., and Ward, E. W. B. (1972) Phytopathol. Z. 74, 141-152
12. Vögeli, U., and Chappell, J. (1988) Plant Physiol. 88, 1291-1296
13. Facchini, P. J., and Chappell, J. (1992) Proc. Natl. Acad. Sci. U. S. A. 89, 11088-11092
14. Ralston, L., Kwon, S. T., Schoenbeck, M., Ralston, J., Schenk, D. J., Coates, R. M., and Chappell, J. (2001) Arch. Biochem. Biophys. 393, 222-235
15. Lupien, S., Karp, F., Wildung, M., and Croteau, R. (1999) Arch. Biochem. Biophys. 368, 181-192
16. Wüst, M., Little, D. B., Schalk, M., and Croteau, R. (2001) Arch. Biochem. Biophys. 387, 125-136
17. Teutsch, H. G., Hasenfratz, M. P., Lesot, A., Stoltz, C., Garnier, J. M., Jeltsch, J. M., Durst, F., and Werck-Reichhart, D. (1993) Proc. Natl. Acad. Sci. U. S. A. 90, 4102-4106
18. Meyer, K., Cusumano, J. C., Somerville, C., and Chapple, C. (1996) Proc. Natl. Acad. Sci. U. S. A. 93, 6869-6874
19. Humphreys, J. M., Hemm, M. R., and Chapple, C. (1999) Proc. Natl. Acad. Sci. U. S. A. 96, 10045-10050
20. Schoendorf, A., Rithner, C. D., Williams, R. M., and Croteau, R. B. (2001) Proc. Natl. Acad. Sci. U. S. A. 98, 1501-1506
21. Jennewein, S., Rithner, C. D., Williams, R. M., and Croteau, R. B. (2001) Proc. Natl. Acad. Sci. U. S. A. 98, 13595-13600
22. Jennewein, S., Rithner, C. D., Williams, R. M., and Croteau, R. (2003) Arch. Biochem. Biophys. 413, 262-270
23. Frey, M., Chomet, P., Glawischnig, E., Stettner, C., Grun, S., Winklmair, A., Eisenreich, W., Bacher, A., Meeley, R. B., Briggs, S. P., Simcox, K., and Gierl, A. (1997) Science 277, 696-699
24. Nomura, T., Ishihara, A., Imaishi, H., Endo, T. R., Ohkawa, H., and Iwamura, H. (2002) Mol. Genet. Genomics 267, 210-217
25. Szekeres, M., Nemeth, K., Koncz-Kalman, Z., Mathur, J., Kauschmann, A., Altmann, T., Redei, G. P., Nagy, F., Schell, J., and Koncz, C. (1996) Cell 85, 171-182
26. Choe, S., Dilkes, B. P., Fujioka, S., Takatsuto, S., Sakurai, A., and Feldmann, K. A. (1998) Plant Cell 10, 231-243
27. Koch, B. M., Sibbesen, O., Halkier, B. A., Svendsen, I., and Moller, B. L. (1995) Arch. Biochem. Biophys. 323, 177-186
28. Kaltenbach, M., Schroder, G., Schmelzer, E., Lutz, V., and Schroder, J. (1999) Plant J. 19, 183-193
29. Menting, J., Scopes, R. K., and Stevenson, T. W. (1994) Plant Physiol. 106, 633-642
30. Xu, Y. L., Li, L., Wu, K., Peeters, A. J., Gage, D. A., and Zeevaart, J. A. (1995) Proc. Natl. Acad. Sci. U. S. A. 92, 6640-6644
31. Phillips, A. L., Ward, D. A., Uknes, S., Appleford, N. E., Lange, T., Huttly, A. K., Gaskin, P., Graebe, J. E., and Hedden, P. (1995) Plant Physiol. 108, 1049-1057
32. Helliwell, C. A., Poole, A., Peacock, W. J., and Dennis, E. S. (1999) Plant Physiol. 119, 507-510
33. Helliwell, C. A., Chandler, P. M., Poole, A., Dennis, E. S., and Peacock, W. J. (2001) Proc. Natl. Acad. Sci. U. S. A. 98, 2065-2070
34. Watson, D. G., Baker, F. C., and Brooks, C. J. W. (1983) Biochem. Soc. Trans. 11, 589-590
35. Whitehead, I. M., Threlfall, D. R., and Ewing, D. F. (1989) Phytochemistry 28, 775-779
36. Williams, P. A., Cosme, J., Sridhar, V., Johnson, E. F., and McRee, D.E. (2000) Mol. Cell 5, 121-131
37. Zhao, Y., Schenk, D. J., Takahashi, S., Chappell, J., and Coates, R. M. (2004) J. Org. Chem. 69, 7428-7435
38. Rising, K. A., Starks, C. M., Noel, J. P., and Chappell, J. (2000) J. Am. Chem. Soc. 122, 1861-1866
39. Pompon, D., Louerat, B., Bronine, A., and Urban, P. (1996) Methods Enzymol. 272, 51-64
40. Urban, P., Mignotte, C., Kazmaier, M., Delorme, F., and Pompon, D. (1997) J. Biol. Chem. 272, 19176-19186
41. Greenhagen, B. T., Griggs, P., Takahashi, S., Ralston, L., and Chappell, J. (2003) Arch. Biochem. Biophys. 409, 385-394
42. Omura, T., and Sato, R. (1964) J. Biol. Chem. 239, 2370-2378
43. Marti-Renom, M. A., Stuart, A., Fiser, A., Sánchez, R., Melo, F., and Sali, A. (2000) Annu. Rev. Biophys. Biomol. Struct. 29, 291-325
44. A. Sali, A., and Blundell, T. L. (1993) J. Mol. Biol. 234, 779-815
45. Fiser, A., Do, R. K., and Sali, A. (2000) Protein Sci. 9, 1753-1773
46. Jones, G., Willett, P., and Glen, R. C. (1995) J. Mol. Biol. 245, 43-53
47. Jones, G., Willett, P., Glen, R. C., Leach, A. R., and Taylor, R. (1997) J. Mol. Biol. 267, 727-748
48. Nissink, J. W. M., Murray, C., Hartshorn, M., Verdonk, M. L., Cole, J. C., and Taylor, R. (2002) Proteins 49, 457-471J. W. M.
49. Verdonk, M. L., Cole, J. C., Hartshorn, M. J., Murray, C. W., and Taylor, R. D. (2003) Proteins 52, 609-623
50. Gotoh, O. (1992) J. Biol. Chem. 267, 83-90
51. Rupasinghe, S., Baudry, J., and Schuler, M. A. (2003) Protein Eng. 16, 721-731
52. He, Y., Luo, Z., Klekotka, P. A., Burnett, V. L., and Halpert, J. R. (1994) Biochemistry 33, 4419-4424
53. Hasler, J. A., Harlow, G. R., Szklarz, G. D., John, G. H., Kedzie, K. M., Burnett, V. L., He, Y. A., Kaminsky, L. S., and Halpert, J. R. (1994) Mol. Pharmacol. 46, 338-345
54. Pelkonen, P., Lang, M. A., Negishi, M., Wild, C. P., and Juvonen, R. O. (1997) Chem. Res. Toxicol. 10, 85-90
55. He, Y. A., He, Y. Q., Szklarz, G. D., and Halpert, J. R. (1997) Biochemistry 22, 8831-8839
56. Schalk, M., and Croteau, R. (2000) Proc. Natl. Acad. Sci. U. S. A. 97, 11948-11953
57. Schoch, G. A., Attias, R., Le Ret, M., and Werck-Reichhart, D. (2003) Eur. J. Biochem. 270, 3684-3695
58. Kedzie, K. M., Balfour, C. A., Escobar, G. Y., Grimm, S. W., He, Y. A., Pepperl, D. J., Regan, J. W., Stevens, J. C., and Halpert, J. R. (1991) J. Biol. Chem. 266, 22515-22521
59. He, Y. A., Balfour, C. A., Kedzie, K. M., and Halpert, J. R. (1992) Biochemistry 31, 9220-9226
60. Khan, K. K., and Halpert, J. R. (2000) Arch. Biochem. Biophys. 373, 335-345
61. Kahn, R. A., Le Bouquin, R., Pinot, F., Benveniste, I., and Durst, F. (2001) Arch. Biochem. Biophys. 15, 180-187
62. Williams, P. A., Cosme, J., Ward, A., Angove, H. C., Matak, V. D., and Jhoti, H. (2003) Nature 424, 464-468
63. Williams, P. A., Cosme, J., Vinkovic, D. M., Ward, A., Angove, H. C., Day, P. J., Vonrhein, C., Tickle, I. J., and Jhoti, H. (2004) Science 305, 683-686
64. Sawada, N., Sakaki, T., Ohta, M., and Inouye, K. (2000) Biochem. Biophys. Res. Commun. 273, 977-984
65. Pikuleva, I., and Javitt, N. B. (2003) Arch. Biochem. Biophys. 420, 35-39
66. Imai, T., Yamazaki, T., and Kominami, S. (1998) Biochemistry 37, 8097-8104
67. Yamazaki, T., Ohno, T., Sakaki, T., Akiyoshi-Shibata, M., Yabusaki, Y., Imai, T., and Kominami, S. (1998) Biochemistry 37, 2800-2806
68. Lewis, D. F. V. (2002) J. Inorg. Biochem. 91, 502-514
69. Kumar, S., Scott, E. E., Liu, H., and Halpert, J. R. (2003) J. Biol. Chem. 278, 17178-17184
70. Wester, M. R., Johnson, E. F., Marques-Soares, C., Dijols, S., Dansette, P. M., Mansuy, D., and Stout, C. D. (2003) Biochemistry 42, 9335-9345
71. Scott, E. E., White, M. A., He, Y. A., Johnson, E. F., Stout, C. D., and Halpert, J. R. (2004) J. Biol. Chem. 279, 27294-27301
72. Wang, E., Wang, R., DeParasis, J., Loughrin, J. H., Gan, S., and Wagner, G. J. (2001) Nat. Biotechnol. 19, 371-374