Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate

Journal of Biological Chemistry

Volumn 275, Issue 19, 2000, Pages 14659-14666

  Wittstock, Ute ^a   Halkier, Barbara Ann ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDOXIME; AMINO ACID; COMPLEMENTARY DNA; CYTOCHROME P450; GLUCOSINOLATE; NUCLEOTIDE; OXYGENASE; PHENYLALANINE; TRYPTOPHAN; TYROSINE;

ARABIDOPSIS; ARTICLE; BIOSYNTHESIS; CATALYSIS; ENZYME ACTIVITY; ENZYME SPECIFICITY; ESCHERICHIA COLI; METABOLISM; NONHUMAN; NUCLEOTIDE SEQUENCE; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL;

AMINO ACID SEQUENCE; ARABIDOPSIS; ARABIDOPSIS PROTEINS; BASE SEQUENCE; CATALYSIS; CLONING, MOLECULAR; CYTOCHROME P-450 ENZYME SYSTEM; DNA, COMPLEMENTARY; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; OXIMES; PHENYLALANINE; PLANTS, GENETICALLY MODIFIED; RECOMBINANT PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID; THIOCYANATES; THIOGLUCOSIDES;

EID: 0034640261     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.275.19.14659     Document Type: Article

References (53)

1. Fenwick, G. R., Heaney, R. K., and Mullin, W. J. (1983) Crit. Rev. Food. Sci. Nutr. 18, 123-201
2. Chew, F. S. (1988) in Biologically Active Natural Products (Cutler, H. G., ed.) pp. 155-181, American Chemical Society, Washington, D.C.
3. Stadler, E. (1978) Entomol. Exp. Appl. 24, 711-720
4. Zhang, Y., Talalay, P., Cho, C. G., and Posner, G. H. (1992) Proc. Natl. Acad. Sci. U. S. A. 89, 2399-2403
5. Hogge, L. R., Reed, D. W., Underhill, E. W., and Haughn, G. W. (1988) J. Chromatogr. 26, 551-556
6. Halkier, B. A. (1999) in Naturally Occurring Glycosides: Chemistry, Distribution and Biological Properties (Ikan, R., ed.) pp. 193-223, John Wiley & Sons Ltd., Chichester, United Kingdom
7. Glendening, T. M., and Poulton, J. E. (1988) Plant Physiol. 86, 319-321
8. Jain, J. C., GrootWassink, J. W. D., Kolenovaky, A. D., and Underhill, E. W. (1990) Phytochemistry 29, 1425-1428
9. Reed, D. W., Davin, L., Jain, J. C., DeLuca, V., Nelson, L., and Underhill, E. W. (1993) Arch. Biochem. Biophys. 305, 526-532
10. Guo, L., and Poulton, J. E. (1994) Phytochemistry 36, 1133-1138
11. Matsuo, M. (1968) Chem. Pharm. Bull. 16, 1128-1129
12. Du, L., and Halkier, B. A. (1997) Trends Plant Sci. 2, 425-431
13. Du, L., Lykkesfeldt, J., Olsen, C. E., and Halkier, B. A. (1995) Proc. Natl. Acad. Sci. U. S. A. 92, 12505-12509
14. Du, L., and Halkier, B. A. (1996) Plant Physiol. 111, 831-837
15. Bennett, R. N., Kiddle, G., and Wallsgrove, R. M. (1997) Photochemistry 45, 59-66
16. Bennett, R. N., Kiddle, G., and Wallsgrove, R. M. (1997) Plant Physiol. 114, 1283-1291
17. Bennett, R., Donald, A., Dawson, G., Hick, A., and Wallsgrove, R. (1993) Plant Physiol. 102, 1307-1312
18. Bennett, R. N., Hick, A. J., Dawson, G. W., and Wallsgrove, R. M. (1995) Plant Physiol. 109, 299-305
19. Bennett, R. N., Kiddle, G., Hick, A. J., Dawson, G. W., and Wallsgrove, R. M. (1996) Plant Cell Environ. 19, 801-812
20. Ludwig-Müller, J., and Hilgenberg, W. (1988) Physiol. Plant. 74, 240-250
21. Sibbesen, O., Koch, B., Halkier, B. A., and Møller, B. L. (1995) J. Biol. Chem. 270, 3506-3511
22. Koch, B., Sibbesen, O., Halkier, B. A., and Møller, B. L. (1995) Arch. Biochem. Biophys. 323, 177-186
23. Nielsen, J. S., and Møller, B. L. (2000) Plant Physiol., in press
24. Andersen, M. D., Busk, P. K., Svendsen, I., and Møller, B. L. (2000) J. Biol. Chem. 275, 1966-1975
25. Bak, S., Nielsen, H. L., and Halkier, B. A. (1998) Plant Mol. Biol. 38, 725-734
26. Hebsgaard, S. M., Korning, P. G., Tolstrup, N., Engelbrecht, J., Rouze, P., and Brunak, S. (1996) Nucleic Acids Res. 24, 3439-3452
27. Barnes, H. (1996) Methods Enzymol. 272, 3-14
28. Barnes, H., Arlotto, M. P., and Watermann, M. R. (1991) Proc. Natl. Acad. Sci. U. S. A. 88, 5597-5601
29. Halkier, B, A., Nielsen, H., Koch, B., and Møller, B. L. (1995) Arch. Biochem. Biophys. 322, 369-377
30. Omura, T., and Sato, R. (1964) J. Biol. Chem. 239, 2370-2378
31. Töpfer, R., Matzeit, V., Gronenborn, B., Schell, J., and Steinbiss, H. H. (1987) Nucleic Acids Res. 15, 5890
32. Hajdukiewicz, P., Svab, Z., and Maliga, P. (1994) Plant Mol. Biol. 25, 989-994
33. Zambryski, P., Genetello, C., Leemans, J., Van Montagu, M., and Schell, J. (1983) EMBO J. 2, 2143-2150
34. Clough, S. J., and Bent, A. F. (1998) Plant J. 16, 735-743
35. Sørensen, H. (1990) in Canola and Rapeseed: Production, Chemistry, Nutrition and Processing Technology (Shahidi, F., ed.) pp. 149-172, Van Nostrand Reinhold, New York,
36. Buchner, R. (1987) in Glucosinolates in Rapeseed: Analytical Aspects (Wathelet, J. P., ed.) pp. 50-58, Martinus Nijhoff Publishers, Kluwer Academic Publishers Group, Dordrecht, The Netherlands
37. Haughn, G. W., Davin, L., Giblin, M., and Underhill, E. W. (1991) Plant Physiol. 97, 217-226
38. Paquette, S. M., Bak, S., and Feyereisen, R. (2000) DNA Cell Biol., in press
39. D'Alessio, J. M., Bebee, R., Hartley, J. L., Noon, M. C., and Polayes, D. (1992) Focus 14, 76-79
40. Olins, P. O., Devine, C. S., Rangwala, S. H., and Kavka, K. S. (1988) Gene (Amst.) 73, 227-235
41. Imai, Y., and Sato, R. (1967) Eur. J. Biochem. 1, 419-426
42. Saupe, S. G. (1981) in Phytochemistry and Angiosperm Phylogeny (Young, D. A., and Seigler, D. S., eds.) pp. 81-116, Praeger Scientific, New York
43. Rodman, J. E., Karol, K. G., Price, R. A., and Sytsma, K. J. (1996) Syst. Bot. 21, 289-307
44. Koch, B., Nielsen, V. S., Halkier, B. A., Olsen, C. E., and Møller, B. L. (1992) Arch. Biochem. Biophys. 292, 141-150
45. Jenkins, C. M., and Waterman, M. R. (1994) J. Biol. Chem. 269, 27401-27408
46. Gillam, E. M. J., Baba, T., Kim, B. R., Ohmori, S., and Guengerich, F. P. (1993) Arch. Biochem. Biophys. 305, 123-131
47. Yun, C. H., Maengseok, S., and Kim. H. (1997) J. Biol. Chem. 272, 19725-19730
48. Pintão, A., Pais, M. S. S., Coley, H., Kelland, L. R., and Judson, I. R. (1995) Planta Med. 61, 233-236
49. Nastruzzi, C., Cortesi, R., Esposito, E., Menegatti, E., Leoni, O., Iori, R., and Palmieri, S. (1996) J. Agric. Food Chem. 44, 1014-1021
50. Manici, L. M., Lazzeri, L., and Palmieri, S. (1997) J. Agric. Food Chem. 45, 2768-2773
51. Fahey, J. W., Zhang, Y., and Talalay, P. (1997) Proc. Natl. Acad. Sci. U. S. A. 94, 10367-10372
52. DellaPenna, D. (1999) Science 285, 375-379
53. Brown, P. D., and Morra, M. (1995) J. Agric. Food Chem. 43, 3070-3074