A stereoselective hydroxylation step of alkaloid biosynthesis by a unique cytochrome P450 in Catharanthus roseus

Journal of Biological Chemistry

Volumn 286, Issue 19, 2011, Pages 16751-16757

  Giddings, Lesley Ann ^a   Liscombe, David K ^a,d   Hamilton, John P ^b   Childs, Kevin L ^b   DellaPenna, Dean ^c   Buell, C Robin ^b   O'Connor, Sarah E ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

^c Michigan State University   (United States)

^d SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID BIOSYNTHESIS; BIOSYNTHETIC GENE; BRANCH POINTS; CANDIDATE GENES; CATALYTIC FUNCTIONS; CATHARANTHUS ROSEUS; CO-EXPRESSION; CYTOCHROME P450; CYTOCHROME P450 GENES; EXPRESSION PROFILE; FUNCTIONAL CHARACTERIZATION; FUNCTIONAL EXPRESSION; INDOLE ALKALOIDS; PHENYLPROPANOIDS; SACCHAROMYCES CEREVISIAE; STEREO-SELECTIVE; TABERSONINE; TERPENOIDS; TRANSCRIPTOMES; VINDOLINE;

BIOCHEMISTRY; BIOSYNTHESIS; ENZYMES; GENE EXPRESSION; HYDROXYLATION; NITROGEN COMPOUNDS; OLEFINS; SCAFFOLDS; YEAST;

METABOLITES;

16 HYDROXYTABERSONINE; 19 HYDROXYTABERSONINE; 19 O ACETYLHORHAMMERICINE; 19 O ACETYLTABERSONINE; 2,3 DIHYDRO 3 HYDROXYTABERSONINE N METHYLTRANSFERASE; ALKALOID; AROMATIC LEVO AMINO ACID DECARBOXYLASE; CYTOCHROME P450; CYTOCHROME P450 71; CYTOCHROME P450 71 BJ1; DEACETYLVINDOLINE ACETYLTRANSFERASE; DESACETOXYVINDOLINE 4 HYDROXYLASE; ECHITOVENINE; GERANIOL; HORHAMMERICINE; LOCHNERICINE; LOGANIC ACID METHYLTRANSFERASE; MINOVINCININE 19 HYDROXY 0 ACETYLTRANSFERASE; SECOLOGANIN; STRICTOSIDINE; TABERSONINE; TRYPTAMINE; UNCLASSIFIED DRUG; VINCADIFFORMINE; VINDOLINE;

ARTICLE; ASPIDOSPERMA; CATHARANTHUS ROSEUS; CLUSTER ANALYSIS; CONTROLLED STUDY; ENZYME ASSAY; ENZYME INHIBITION; ENZYME KINETICS; ENZYME SPECIFICITY; EXPRESSED SEQUENCE TAG; GENE EXPRESSION PROFILING; GENE IDENTIFICATION; HYDROXYLATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; PLANT GENETICS; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN SYNTHESIS; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY;

ALKALOIDS; CATHARANTHUS; CLONING, MOLECULAR; CLUSTER ANALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; GENE EXPRESSION PROFILING; HYDROXYLATION; INDOLE ALKALOIDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, BIOLOGICAL; MOLECULAR SEQUENCE DATA; PLANT PROTEINS; QUINOLINES; SACCHAROMYCES CEREVISIAE; STEREOISOMERISM; VINBLASTINE;

ASPIDOSPERMA; CATHARANTHUS ROSEUS; SACCHAROMYCES CEREVISIAE;

EID: 79955772476     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M111.225383     Document Type: Article

References (29)

1. Nielsen, K. A., Moller, B. L. (2005) in Cytochrome P450: Structure, Mechanism, and Biochemistry (de Montellano, P. R., ed.), 3rd Ed., pp. 553-583, Kluwer Academic/Plenum Publishers, New York
2. Jensen, K., and Møller, B. L. (2010) Phytochemistry 71, 132-141
3. Nelson, D. R., Schuler, M. A., Paquette, S. M., Werck-Reichhart, D., and Bak, S. (2004) Plant Physiol. 135, 756-772
4. Mizutani, M., and Ohta, D. (2010) Annu. Rev. Plant Biol. 61, 291-315
5. O'Connor, S. E., and Maresh, J. J. (2006) Nat. Prod. Rep. 23, 532-547
6. Laflamme, P., St-Pierre, B., and De Luca, V. (2001) Plant Physiol. 125, 189-198
7. Furuya, T., Sakamoto, K., Iida, K., Asada, Y., Yoshikawa, T., Sakai, S., and Aimi, N. (1992) Phytochemistry 31, 3065-3068
8. Shanks, J. V., Bhadra, R., Morgan, J., Rijhwani, S., and Vani, S. (1998) Biotechnol. Bioeng. 58, 333-338
9. Kutney, J. P., Choi, L. S., Kolodziejczyk, P., Sleigh, S. K., Stuart, K. L., Worth, B. R., Kurz, W. G., Chatson, K. B., and Constabel, F. (1980) Phytochemistry 19, 2589-2595
10. Morgan, J. A., and Shanks, J. V. (1999) Phytochemistry 51, 61-68
11. Facchini, P. J., and De Luca, V. (2008) Plant J. 54, 763-784
12. Kaltenbach, M., Schröder, G., Schmelzer, E., Lutz, V., and Schröder, J. (1999) Plant J. 19, 183-193
13. Hotze, M., Schröder, G., and Schröder, J. (1995) FEBS Lett. 374, 345-350
14. Collu, G., Unver, N., Peltenburg-Looman, A. M., van der Heijden, R., Verpoorte, R., and Memelink, J. (2001) FEBS Lett. 508, 215-220
15. Irmler, S., Schröder, G., St-Pierre, B., Crouch, N. P., Hotze, M., Schmidt, J., Strack, D., Matern, U., and Schröder, J. (2000) Plant J. 24, 797-804
16. Schröder, G., Unterbusch, E., Kaltenbach, M., Schmidt, J., Strack, D., De Luca, V., and Schröder, J. (1999) FEBS Lett. 458, 97-102
17. Ehlting, J., Sauveplane, V., Olry, A., Ginglinger, J. F., Provart, N. J., and Werck-Reichhart, D. (2008) BMC Plant Biol. 8, 47
18. Matsuno, M., Compagnon, V., Schoch, G. A., Schmitt, M., Debayle, D., Bassard, J. E., Pollet, B., Hehn, A., Heintz, D., Ullmann, P., Lapierre, C., Bernier, F., Ehlting, J., and Werck-Reichhart, D. (2009) Science 325, 1688-1692
19. Zerbino, D. R., and Birney, E. (2008) Genome Res. 18, 821-829
20. Langmead, B., Trapnell, C., Pop, M., and Salzberg, S. L. (2009) Genome Biol. 10, R25
21. Saldanha, A. J. (2004) Bioinformatics 20, 3246-3248
22. Pompon, D., Louerat, B., Bronine, A., and Urban, P. (1996) Methods Enzymol. 272, 51-64
23. Gietz, R. D., and Woods, R. A. (2002) Methods Enzymol. 350, 87-96
24. Hisiger, S., and Jolicoeur, M. (2007) Phytochem. Rev. 6, 207-234
25. Abraham, D. J., Farnsworth, N. R., Loub, W. D., and Blomster, R. N. (1969) J. Org. Chem. 34, 1575-1576
26. Liscombe, D. K., Usera, A. R., and O'Connor, S. E. (2010) Proc. Natl. Acad. Sci. U.S.A. 107, 18793-18798
27. Rodriguez, S., Compagnon, V., Crouch, N. P., St-Pierre, B., and De Luca, V. (2003) Phytochemistry 64, 401-409
28. Langlois, N., and Andriamialisoa, R. Z. (1979) J. Org. Chem. 44, 2468-2471
29. Kohl, W., Witte, B., and Hofle, G. (1981) Z. Naturforsch. B 36, 1153-1162