A single amino acid substitution (F363I) converts the regiochemistry of the spearmint (-)-limonene hydroxylase from a C6- to a C3-hydroxylase

Proceedings of the National Academy of Sciences of the United States of America

Volumn 97, Issue 22, 2000, Pages 11948-11953

  Schalk, Michel ^a   Croteau, Rodney ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

Cytochrome P450; Mentha; Mint; Monoterpene; Trans carveol; Trans isopiperitenol

Indexed keywords

COMPLEMENTARY DNA; CYTOCHROME P450; ESSENTIAL OIL; ISOLEUCINE; LIMONENE HYDROXYLASE; OXYGEN; OXYGENASE; PEPPERMINT; PHENYLALANINE; TERPENE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; CONTROLLED STUDY; ENZYME KINETICS; ENZYME SPECIFICITY; ENZYME STRUCTURE; HYDROXYLATION; NONHUMAN; PRIORITY JOURNAL; SEQUENCE HOMOLOGY; SITE DIRECTED MUTAGENESIS; SPEARMINT; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; CYTOCHROME P-450 ENZYME SYSTEM; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; POLYMERASE CHAIN REACTION; SEQUENCE HOMOLOGY, AMINO ACID;

MENTHA; MENTHA SPICATA; MENTHA X PIPERITA;

EID: 0034710909     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.97.22.11948     Document Type: Article

References (37)

1. Lawrence, B. M. (1981) in Essential Oils, eds. Mookherjee, B. D. & Mussinan, C. J. (Allured Press, Wheaton, IL), pp. 1-81.
2. Croteau, R. & Gershenzon, J. (1994) Recent Adv. Phytochem. 28, 193-229.
3. Karp, F., Mihaliak, C. A., Harris, J. L. & Croteau, R. (1990) Arch. Biochem. Biophys. 276, 219-226.
4. Lupien, S., Karp, F., Wildung, M. & Croteau, R. (1999) Arch. Biochem. Biophys. 368, 181-192.
5. Nelson, D. R., Koymans, L., Kamataki, T., Stegeman, J. J., Feyereisen, R., Waxman, D. J., Waterman, M. R., Gotoh, O., Coon, M. J., Estabrook, R. J., et al. (1996) Pharmacogenetics 6, 1-42.
6. Haudenschild, C., Schalk, M., Karp, F. & Croteau, R. (2000) Arch. Biochem. Biophys. 379, 127-136.
7. Poulos, T. L., Finzel, B. C. & Howard, A. J. (1987) J. Mol. Biol. 195, 687-700.
8. Ravichandran, K. G., Boddupalli, S. S., Hasemann, C. A., Peterson, J. A. & Deisenhofer, J. (1993) Science 261, 731-736.
9. Hasemann, C. A., Ravichandran, K. G., Peterson, J. A. & Deisenhofer, J. (1994) J. Mol. Biol. 236, 1169-1185.
10. Cupp-Vickery, J. R. & Poulos, T. L. (1995) Nat. Struct. Biol. 2, 144-153.
11. Park, S. Y., Shimizu, H., Adachi, S., Nakagawa, A., Tanaka, I., Nakahara, K., Shoun, H., Obayashi, E., Nakamura, H., Iizura, T., et al. (1997) Nat. Struct. Biol. 4, 827-832.
12. von Wachenfeldt, C. & Johnson, E. F. (1995) in Cytochrome P450: Structure, Mechanism and Biochemistry, 2nd Ed., ed. Ortiz de Montellano, P. (Plenum Press, New York), pp. 183-223.
13. Negishi, M., Uno, T., Darden, T. A., Sueyoshi, T. & Pedersen, L. G. (1996) FASEB J. 10, 683-689.
14. He, Y. Q., Szklarz, G. D. & Halpert, J. R. (1996) Arch. Biochem. Biophys. 335, 152-160.
15. Böttner, B., Denner, K. & Bernhardt, R. (1998) Eur. J. Biochem. 252, 458-466.
16. Zimmer, T., Scheller, U., Takagi, M. & Schunck, W.-H. (1998) Eur. J. Biochem. 256, 398-403.
17. Lindberg, R. L. P. & Negishi, M. (1989) Nature (London) 339, 632-634.
18. Iwasaki, M., Darden, T. A., Pedersen, L. G. & Negishi, M. (1995) Biochemistry 34, 5056-5059.
19. Ellis, S. W., Rowland, K., Ackland, M. J., Rekka, E., Simula, A. P., Lennard, M. S., Wolf, C. R. & Tucker, G. T. (1996) Biochem. J. 316, 647-654.
20. Hanna, I. H., Roberts, E. S. & Hollenberg, P. F. (1998) Biochemistry 37, 311-318.
21. He, Y. A., He, Y. Q., Szklarz, G. D. & Halpert, J. R. (1997) Biochemistry 36, 8831-8839.
22. Richardson, T. H. & Johnson, E. F. (1994) J. Biol. Chem. 269, 23937-23943.
23. He, Y. Q., Harlow, G. R., Szklarz, G. D. & Halpert, J. R. (1998) Arch. Biochem. Biophys. 350, 333-339.
24. Dierks, E. A., Davis, S. C. & Ortiz de Montellano, P. R. (1998) Biochemistry 37, 1839-1847.
25. Hasemann, C. A., Kurumbail, R. G., Boddupalli, S. S., Peterson, J. A. & Deisenhofer, J. (1995) Structure 3, 41-62.
26. Graham, S. E. & Peterson, J. A. (1999) Arch. Biochem. Biophys. 369, 24-29.
27. Gotoh, O. (1992) J. Biol. Chem. 267, 83-90.
28. Barnes, H. J. (1996) Methods Enzymol. 272B, 3-14.
29. Horton, R. M., Hunt, H. D., Ho, S. N., Pullen, J. K. & Pease, L. R. (1989) Gene 77, 61-68.
30. Devereux, J., Haeberlin, P. & Smithies, O. (1994) Nucleic Acids Res. 12, 387-395.
31. Sali, A. & Blundell, T. L. (1993) J. Mol. Biol. 234, 779-815.
32. Raag, R. & Poulos, T. L. (1989) Biochemistry 28, 917-922.
33. Jefcoate, C. R. (1978) Methods Enzymol. 52, 258-279.
34. Peterson, J. A. & Graham-Lorence, S. E. (1995) in Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd Ed., ed. Ortiz de Montellano, P. R. (Plenum Press, New York), pp. 151-180.
35. Williams, P. A., Cosme, J., Sridhar, V., Johnson, E. F. & McRee, D. E. (2000) Mol. Cell 5, 121-131.
36. Graham-Lorence, S. E. & Peterson, J. A. (1996) Methods Enzymol. 272B, 315-326.
37. Kraulis, P. J. (1991) J. Appl. Crystallogr. 24, 946-950.