Enzymatic 13C labeling and multidimensional NMR analysis of miltiradiene synthesized by bifunctional diterpene cyclase in Selaginella moellendorffii

Journal of Biological Chemistry

Volumn 286, Issue 50, 2011, Pages 42840-42847

  Sugai, Yoshinori ^a   Ueno, Yohei ^a   Hayashi, Ken Ichiro ^b   Oogami, Shingo ^b   Toyomasu, Tomonobu ^c   Matsumoto, Sadamu ^d   Natsume, Masahiro ^a   Nozaki, Hiroshi ^b   Kawaide, Hiroshi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^c YAMAGATA UNIVERSITY   (Japan)

^d DEPARTMENT OF BOTANY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIFUNCTIONAL; BIOSYNTHETIC PRECURSORS; CARBON SKELETON; CHINESE MEDICINAL HERBS; CYCLASE ACTIVITY; CYCLASES; CYCLIZATION REACTIONS; DIPHOSPHATES; DITERPENE CYCLASES; DITERPENE HYDROCARBONS; DITERPENES; GERANYLGERANYL DIPHOSPHATE; HYDROCARBON PRODUCT; MEVALONATE; MONOFUNCTIONAL; MULTIDIMENSIONAL NMR; NMR ANALYSIS; NMR SPECTROSCOPIC ANALYSIS; SALVIA MILTIORRHIZA; SYNTHASES;

BIOCHEMISTRY; BIOSYNTHESIS; CARBON; CLONING; GENES; ISOTOPES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; ORGANIC COMPOUNDS; REACTION INTERMEDIATES; SPECTROSCOPIC ANALYSIS;

CYCLIZATION;

BIFUNCTIONAL DITERPENE CYCLASE; CARBON 13; COMPLEMENTARY DNA; COPALYL DIPHOSPHATE; DITERPENE HYDROCARBON; GERANYLGERANYL PYROPHOSPHATE; HYDROCARBON; LYASE; MEVALONIC ACID; MILTIRADIENE; NATURAL PRODUCT; PROTEIN SMMDS; PYROPHOSPHATE; SYNTHETASE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CONTROLLED STUDY; CYCLIZATION; ENZYME ACTIVITY; IONIZATION; ISOTOPE LABELING; MOLECULAR CLONING; MUTATION; NONHUMAN; PLANT GENE; PLANT GENOME; PRIORITY JOURNAL; PROTEIN MOTIF; PROTON TRANSPORT; SELAGINELLA; SELAGINELLA MOELLENDORFFII;

CARBON ISOTOPES; MAGNETIC RESONANCE SPECTROSCOPY; PLANT PROTEINS; POLYISOPRENYL PHOSPHATES; SELAGINELLACEAE; TERPENES;

EID: 83355166952     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M111.302703     Document Type: Article

References (38)

1. MacMillan, J., and Beale, M. H. (1999) Comprehensive Natural Product Chemistry, pp. 217-243, Elsevier Science Ltd., Oxford
2. Trapp, S., and Croteau, R. (2001) Annu. Rev. Plant Physiol. Plant Mol. Biol. 52, 689-724
3. Toyomasu, T., and Sassa, T. (2010) Comprehensive Natural Product II Chemistry and Biology, pp. 643-672, Elsevier, Oxford
4. Hayashi, K., Kawaide, H., Notomi, M., Sakigi, Y., Matsuo, A., and Nozaki, H. (2006) FEBS Lett. 580, 6175-6181
5. Kawaide, H., Hayashi, K., Kawanabe, R., Sakigi, Y., Matsuo, A., Natsume, M., and Nozaki, H. (2011) FEBS J. 278, 123-133
6. Kawaide, H., Imai, R., Sassa, T., and Kamiya, Y. (1997) J. Biol. Chem. 272, 21706-21712
7. Toyomasu, T., Kawaide, H., Ishizaki, A., Shinoda, S., Otsuka, M., Mitsuhashi, W., and Sassa, T. (2000) Biosci. Biotechnol. Biochem. 64, 660-664
8. Kawaide, H. (2006) Biosci. Biotechnol. Biochem. 70, 583-590
9. Vogel, B. S., Wildung, M. R., Vogel, G., and Croteau, R. (1996) J. Biol. Chem. 271, 23262-23268
10. Martin, D. M., Fäldt, J., and Bohlmann, J. (2004) Plant Physiol. 135, 1908-1927
11. Köksal, M., Jin, Y., Coates, R. M., Croteau, R., and Christianson, D. W. (2011) Nature 469, 116-120
12. Köksal, M., Hu, H., Coates, R. M., Peters, R. J., and Christianson, D. W. (2011) Nat. Chem. Biol. 7, 431-433
13. Wilderman, P. R., and Peters, R. J. (2007) J. Am. Chem. Soc. 129, 15736-15737
14. Claridge, T. D. W. (2009) High-Resolution NMR Techniques in Organic Chemistry, 2nd Ed., pp. 189-232, Elsevier, Oxford
15. Sugai, Y., Miyazaki, S., Mukai, S., Yumoto, I., Natsume, M., and Kawaide, H. (2011) Biosci. Biotechnol. Biochem. 75, 128-135
16. Banks, J. A., Nishiyama, T., Hasebe, M., Bowman, J. L., Gribskov, M., dePamphilis, C., Albert, V. A., Aono, N., Aoyama, T., Ambrose, B. A., Ashton, N. W., Axtell, M. J., Barker, E., Barker, M. S., Bennetzen, J. L., Bonawitz, N. D., Chapple, C., Cheng, C., Correa, L. G., Dacre, M., DeBarry, J., Dreyer, I., Elias, M., Engstrom, E. M., Estelle, M., Feng, L., Finet, C., Floyd, S. K., Frommer, W. B., Fujita, T., Gramzow, L., Gutensohn, M., Harholt, J., Hattori, M., Heyl, A., Hirai, T., Hiwatashi, Y., Ishikawa, M., Iwata, M., Karol, K. G., Koehler, B., Kolukisaoglu, U., Kubo, M., Kurata, T., Lalonde, S., Li, K., Li, Y., Litt, A., Lyons, E., Manning, G., Maruyama, T., Michael, T. P., Mikami, K., Miyazaki, S., Morinaga, S., Murata, T., Mueller- Roeber, B., Nelson, D. R., Obara, M., Oguri, Y., Olmstead, R. G., Onodera, N., Petersen, B. L., Pils, B., Prigge, M., Rensing, S. A., Riaño-Pachón, D. M., Roberts, A. W., Sato, Y., Scheller, H. V., Schulz, B., Schulz, C., Shakirov, E. V., Shibagaki, N., Shinohara, N., Shippen, D. E., Sørensen, I., Sotooka, R., Sugimoto, N., Sugita, M., Sumikawa, N., Tanurdzic, M., Theissen, G., Ulvskov, P., Wakazuki, S., Weng, J. K., Willats, W. W., Wipf, D., Wolf, P. G., Yang, L., Zimmer, A. D., Zhu, Q., Mitros, T., Hellsten, U., Loqué, D., Otillar, R., Salamov, A., Schmutz, J., Shapiro, H., Lindquist, E., Lucas, S., Rokhsar, D., and Grigoriev, I. V. (2011) Science 332, 960-963
17. Chen, F., Tholl, D., Bohlmann, J., and Pichersky, E. (2011) Plant J. 66, 212-229
18. Hirano, K., Nakajima, M., Asano, K., Nishiyama, T., Sakakibara, H., Kojima, M., Katoh, E., Xiang, H., Tanahashi, T., Hasebe, M., Banks, J. A., Ashikari, M., Kitano, H., Ueguchi-Tanaka, M., and Matsuoka, M. (2007) Plant Cell 19, 3058-3079
19. Gao, W., Hillwig, M. L., Huang, L., Cui, G., Wang, X., Kong, J., Yang, B., and Peters, R. J. (2009) Org. Lett. 11, 5170-5173
20. Breeze, A. L. (2000) Prog. Nucl. Magn. Reson. Spectrosc. 36, 323-372
21. Willker, W., Leibfritz, D., Kerssebaum, R., and Bermel, W. (1993) Magn. Reson. Chem. 31, 287-292
22. Vuister, G. W., and Bax, A. (1992) J. Magn. Reson. 98, 428-435
23. Nagayama, K., Kumar, A., Wüthrich, K., and Ernst, R. R. (1980) J. Magn. Reson. 40, 321-334
24. Bax, A., Clore, G. M., and Gronenborn, A. M. (1990) J. Magn. Reson. 88, 425-431
25. Gehring, K., and Ekiel, I. (1998) J. Magn. Reson. 135, 185-193
26. Johnson, B. A. (2004) Methods Mol. Biol. 278, 313-352
27. Kobayashi, N., Iwahara, J., Koshiba, S., Tomizawa, T., Tochio, N., Güntert, P., Kigawa, T., and Yokoyama, S. (2007) J. Biomol. NMR 39, 31-52
28. Sun, T. P., and Kamiya, Y. (1994) Plant Cell 6, 1509-1518
29. Yamaguchi, S., Sun, T., Kawaide, H., and Kamiya, Y. (1998) Plant Physiol. 116, 1271-1278
30. Otomo, K., Kenmoku, H., Oikawa, H., König, W. A., Toshima, H., Mitsuhashi, W., Yamane, H., Sassa, T., and Toyomasu, T. (2004) Plant J. 39, 886-893
31. Toyomasu, T., Niida, R., Kenmoku, H., Kanno, Y., Miura, S., Nakano, C., Shiono, Y., Mitsuhashi, W., Toshima, H., Oikawa, H., Hoshino, T., Dairi, T., Kato, N., and Sassa, T. (2008) Biosci. Biotechnol. Biochem. 72, 1038-1047
32. Mafu, S., Hillwig, M. L., and Peters, R. J. (2011) ChemBioChem 12, 1984-1987
33. Richman, A. S., Gijzen, M., Starratt, A. N., Yang, Z., and Brandle, J. E. (1999) Plant J. 19, 411-421
34. Yamane, H., Satoh, Y., Nohara, K., Nakayama, M., Murofushi, N., Takahashi, N., Takeno, K., Furuya, M., Furber, M., and Mander, L. N. (1988) Tetrahedron Lett. 29, 3959-3962
35. Keeling, C. I., Dullat, H. K., Yuen, M., Ralph, S. G., Jancsik, S., and Bohlmann, J. (2010) Plant Physiol. 152, 1197-1208
36. Keeling, C. I., Madilao, L. L., Zerbe, P., Dullat, H. K., and Bohlmann, J. (2011) J. Biol. Chem. 286, 21145-21153
37. Peters, R. J., Flory, J. E., Jetter, R., Ravn, M. M., Lee, H. J., Coates, R. M., and Croteau, R. B. (2000) Biochemistry 39, 15592-15602
38. Zhou, K., and Peters, R. J. (2009) Phytochemistry 70, 366-369