Protonation of a neutral (S)-β-bisabolene intermediate is involved in (S)-β-macrocarpene formation by the maize sesquiterpene synthases TPS6 and TPS11

Journal of Biological Chemistry

Volumn 283, Issue 30, 2008, Pages 20779-20788

  Köllner, Tobias G ^a   Schnee, Christiane ^a   Li, Shenghong ^a   Svatoš, Aleš ^a   Schneider, Bernd ^a   Gershenzon, Jonathan ^a   Degenhardt, Jörg ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSTS; OLEFINS; PROTEINS; PROTONATION; SIGNAL TRANSDUCTION;

ACTIVE CENTERS; BISABOLENE; CARBON SKELETONS; COFACTOR; DIPHOSPHATE; HERBIVORE DAMAGES; IN PLANTS; LONG DISTANCES; MAIZE GENES; MULTIPLE PRODUCTS; MUTATIONAL ANALYSIS; REACTION MECHANISMS; REPROTONATION; SESQUITERPENE; SYNTHASES; TERPENE SYNTHASES; TYROSINE RESIDUES;

ENZYMES;

ALKENE; BETA BISABOLENE; BETA MACROCARPENE; MAGNESIUM ION; PLANT DNA; PLANT RNA; SESQUITERPENE; SESQUITERPENE SYNTHASE; SYNTHETASE; TYROSINE; UNCLASSIFIED DRUG; WATER; BETA-BISABOLENE; BETA-MACROCARPENE; GLUCOSYLTRANSFERASE; MAGNESIUM; PROTON; TERPENE SYNTHASE; TRANSFERASE;

ARTICLE; BIOSYNTHESIS; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME SUBSTRATE; EXTRACTION; GENE AMPLIFICATION; GENE EXPRESSION REGULATION; GENE ISOLATION; GENE MAPPING; GENE OVEREXPRESSION; GENE TPS11; GENE TPS6; GENETIC CODE; GENETIC CONSERVATION; GENETIC TRANSCRIPTION; HERBIVORE; LEAF DAMAGE; MAIZE; MUTATIONAL ANALYSIS; NONHUMAN; NUCLEOTIDE SEQUENCE; PH; PLANT GENE; PLANT GENETICS; PLANT LEAF; PLANT ROOT; PRIORITY JOURNAL; PROTON TRANSPORT; RNA HYBRIDIZATION; SIGNAL TRANSDUCTION; SITE DIRECTED MUTAGENESIS; UPREGULATION; AMINO ACID SEQUENCE; ANIMAL; CHEMISTRY; ENZYMOLOGY; METABOLISM; MOLECULAR GENETICS; SEQUENCE HOMOLOGY;

ZEA MAYS;

ALKYL AND ARYL TRANSFERASES; AMINO ACID SEQUENCE; ANIMALS; DNA MUTATIONAL ANALYSIS; GENE EXPRESSION REGULATION, PLANT; GLUCOSYLTRANSFERASES; HYDROGEN-ION CONCENTRATION; MAGNESIUM; MOLECULAR SEQUENCE DATA; PLANT LEAVES; PLANT ROOTS; PROTONS; SEQUENCE HOMOLOGY, AMINO ACID; SESQUITERPENES; ZEA MAYS;

EID: 51049091699     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M802682200     Document Type: Article

References (35)

1. Gershenzon, J., and Kreis, W. (1999) Biochemistry of Plant Secondary Metabolism: Annual Plant Reviews, Vol. 2, pp. 222-299, Sheffield Academic Press, Sheffield, UK
2. Croteau, R. (1987) Chem. Rev. 87, 929-954
3. Cane, D. E. (1990) Chem. Rev. 90, 1089-1103
4. Steele, C. L., Crock, J., Bohlmann, J., and Croteau, R. (1998) J. Biol. Chem. 273, 2078-2089
5. Cane, D. E. (1999) Comprehensive Natural Products Chemistry, Vol. 2, pp. 155-200, Elsevier, Amsterdam
6. Cane, D. E., Prabhakaran, P. C., Oliver, J. S., and McIlwaine, D. B. (1990) J. Am. Chem. Soc. 112, 3209-3210
7. Facchini, P. J., and Chappell, J. (1992) Proc. Natl. Acad. Sci. U. S. A. 89, 11088-11092
8. Starks, C. M., Back, K. W., Chappell, J., and Noel, J. P. (1997) Science 277, 1815-1820
9. Rising, K. A., Starks, C. M., Noel, J. P., and Chappell, J. (2000) J. Am. Chem. Soc. 122, 1861-1866
10. Back, K., and Chappell, J. (1995) J. Biol. Chem. 270, 7375-7381
11. Sharon-Asa, L., Shalit, M., Frydman, A., Bar, E., Holland, D., Or, E., Lavi, U., Lewinsohn, E., and Eyal, Y. (2003) Plant J. 36, 664-674
12. Iijima, Y., Davidovich-Rikanati, R., Fridman, E., Gang, D. R., Bar, E., Lewinsohn, E., and Pichersky, E. (2004) Plant Physiol. 136, 3724-3736
13. Rasmann, S., Kollner, T. G., Degenhardt, J., Hiltpold, I., Toepfer, S., Kuhlmann, U., Gershenzon, J., and Turlings, T. C. J. (2005) Nature 434, 732-737
14. Schnee, C., Kollner, T. G., Held, M., Turlings, T. C. J., Gershenzon, J., and Degenhardt, J. (2006) Proc. Natl. Acad. Sci. U. S. A. 103, 1129-1134
15. Kollner, T. G., Held, M., Lenk, C., Hiltpold, I., Turlings, T. C. J., Gershenzon, J., and Degenhardt, J. (2008) Plant Cell 20, 482-494
16. Degenhardt, J., and Gershenzon, J. (2000) Planta 210, 815-822
17. Burr, B., and Burr, F. A. (1991) Trends Genet. 7, 55-60
18. Kollner, T. G., Schnee, C., Gershenzon, J., and Degenhardt, J. (2004) Plant Cell 16, 1115-1131
19. Konig, W. A., Rieck, A., Hardt, I., Gehrcke, B., Kubeczka, K. H., and Muhle, H. (1994) J. High Resolut. Chromatogr. 17, 315-320
20. Cool, L. G. (2005) Phytochemistry 66, 249-260
21. Schnee, C., Kollner, T. G., Gershenzon, J., and Degenhardt, J. (2002) Plant Physiol. 130, 2049-2060
22. Basse, C. W. (2005) Plant Physiol. 138, 1774-1784
23. Marschener, H. (1998) Field Crops Res. 56, 203-207
24. Crock, J., Wildung, M., and Croteau, R. (1997) Proc. Natl. Acad. Sci. U. S. A. 94, 12833-12838
25. Picaud, S., Olofsson, L., Brodelius, M., and Brodelius, P. E. (2005) Arch. Biochem. Biophys. 436, 215-226
26. Kollner, T. G., O'Maille, P. E., Gatto, N., Boland, W., Gershenzon, J., and Degenhardt, J. (2006) Arch. Biochem. Biophys. 448, 83-92
27. Xu, M. M., Wilderman, P. R., and Peters, R. J. (2007) Proc. Natl. Acad. Sci. U. S. A. 104, 7397-7401
28. Allemann, R. K., Young, N. J., Ma, S., Truhlar, D. G., and Gao, J. (2007) J. Am. Chem. Soc. 129, 13008-13013
29. Shishova, E. Y., Di Costanzo, L., Cane, D. E., and Christianson, D. W. (2007) Biochemistry 46, 1941-1951
30. Little, D. B., and Croteau, R. B. (2002) Arch. Biochem. Biophys. 402, 120-135
31. MacMillan, J. (1997) Nat. Prod. Rep. 14, 221-243
32. Aubourg, S., Lecharny, A., and Bohlmann, J. (2002) Mol. Genet. Genom. 267, 730-745
33. Yuan, Y. S., Kollner, T. G., Wiggins, G., Grant, J., Degenhardt, J., and Chen, F. (2008) Plant J., in press
34. Kollner, T. G., Schnee, C., Gershenzon, J., and Degenhardt, J. (2004) Phytochemistry 65, 1895-1902
35. Erb, M., Ton, J., Degenhardt, J., and Turlings, T. C. J. (2008) Plant Physiol. 146, 867-874