Molecular Basis for Stellatic Acid Biosynthesis: A Genome Mining Approach for Discovery of Sesterterpene Synthases

Organic Letters

Volumn 17, Issue 18, 2015, Pages 4644-4647

  Matsuda, Yudai ^a   Mitsuhashi, Takaaki ^a   Quan, Zhiyang ^a   Abe, Ikuro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SESTERTERPENE; STELLATA-2,6,19-TRIENE; STELLATIC ACID; TERPENE SYNTHASE; TRANSFERASE;

CHEMICAL STRUCTURE; CHEMISTRY; EMERICELLA; ENZYMOLOGY; GENETICS; ISOLATION AND PURIFICATION; METABOLISM;

ALKYL AND ARYL TRANSFERASES; EMERICELLA; MOLECULAR STRUCTURE; SESTERTERPENES;

EID: 84941882831     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02404     Document Type: Article

References (24)

1. Christianson, D. W. Chem. Rev. 2006, 106, 3412 10.1021/cr050286w
2. Gao, Y.; Honzatko, R. B.; Peters, R. J. Nat. Prod. Rep. 2012, 29, 1153-1175 10.1039/c2np20059g
3. Wang, L.; Yang, B.; Lin, X.-P.; Zhou, X.-F.; Liu, Y. Nat. Prod. Rep. 2013, 30, 455-473 10.1039/c3np20089b
4. Chiba, R.; Minami, A.; Gomi, K.; Oikawa, H. Org. Lett. 2013, 15, 594-597 10.1021/ol303408a
5. Toyomasu, T.; Tsukahara, M.; Kaneko, A.; Niida, R.; Mitsuhashi, W.; Dairi, T.; Kato, N.; Sassa, T. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 3084-3088 10.1073/pnas.0608426104
6. Toyomasu, T.; Kaneko, A.; Tokiwano, T.; Kanno, Y.; Kanno, Y.; Niida, R.; Miura, S.; Nishioka, T.; Ikeda, C.; Mitsuhashi, W. J. Org. Chem. 2009, 74, 1541-1548 10.1021/jo802319e
7. Sato, T.; Yamaga, H.; Kashima, S.; Murata, Y.; Shinada, T.; Nakano, C.; Hoshino, T. ChemBioChem 2013, 14, 822-825 10.1002/cbic.201300035
8. Ueda, D.; Yamaga, H.; Murakami, M.; Totsuka, Y.; Shinada, T.; Sato, T. ChemBioChem 2015, 16, 1371-1377 10.1002/cbic.201500138
9. Hensens, O. D.; Zink, D.; Williamson, J. M.; Lotti, V. J.; Chang, R. S.; Goetz, M. A. J. Org. Chem. 1991, 56, 3399-3403 10.1021/jo00010a040
10. Wei, H.; Itoh, T.; Kinoshita, M.; Nakai, Y.; Kurotaki, M.; Kobayashi, M. Tetrahedron 2004, 60, 6015-6019 10.1016/j.tet.2004.05.021
11. Sadler, I. H.; Simpson, T. J. J. Chem. Soc., Chem. Commun. 1989, 1602-1604 10.1039/c39890001602
12. Singh, S. B.; Reamer, R.; Zink, D.; Schmatz, D.; Dombrowski, A.; Goetz, M. J. Org. Chem. 1991, 56, 5618-5622 10.1021/jo00019a030
13. Qureshi, I. H.; Husain, S. A.; Noorani, R.; Murtaza, N.; Iitaka, Y.; Iwasaki, S.; Okuda, S. Tetrahedron Lett. 1980, 21, 1961-1962 10.1016/S0040-4039(00)93657-8
14. Liangsakul, J.; Pornpakakul, S.; Sangvichien, E.; Muangsin, N.; Sihanonth, P. Tetrahedron Lett. 2011, 52, 6427-6430 10.1016/j.tetlet.2011.09.079
15. Matsuda, Y.; Wakimoto, T.; Mori, T.; Awakawa, T.; Abe, I. J. Am. Chem. Soc. 2014, 136, 15326-15336 10.1021/ja508127q
16. Shishova, E. Y.; Di Costanzo, L.; Cane, D. E.; Christianson, D. W. Biochemistry 2007, 46, 1941-1951 10.1021/bi0622524
17. Baer, P.; Rabe, P.; Fischer, K.; Citron, C. A.; Klapschinski, T. A.; Groll, M.; Dickschat, J. S. Angew. Chem., Int. Ed. 2014, 53, 7652-7656 10.1002/anie.201403648
18. Jin, F. J.; Maruyama, J.; Juvvadi, P. R.; Arioka, M.; Kitamoto, K. FEMS Microbiol. Lett. 2004, 239, 79-85 10.1016/j.femsle.2004.08.025
19. Matsuda, Y.; Iwabuchi, T.; Wakimoto, T.; Awakawa, T.; Abe, I. J. Am. Chem. Soc. 2015, 137, 3393-3401 10.1021/jacs.5b00570
20. Liu, C.; Tagami, K.; Minami, A.; Matsumoto, T.; Frisvad, J. C.; Suzuki, H.; Ishikawa, J.; Gomi, K.; Oikawa, H. Angew. Chem., Int. Ed. 2015, 54, 5748-5752 10.1002/anie.201501072
21. Caniard, A.; Zerbe, P.; Legrand, S.; Cohade, A.; Valot, N.; Magnard, J.-L.; Bohlmann, J.; Legendre, L. BMC Plant Biol. 2012, 12, 119 10.1186/1471-2229-12-119
22. Ro, D. K.; Paradise, E. M.; Ouellet, M.; Fisher, K. J.; Newman, K. L.; Ndungu, J. M.; Ho, K. A.; Eachus, R. A.; Ham, T. S.; Kirby, J.; Chang, M. C. Y.; Withers, S. T.; Shiba, Y.; Sarpong, R.; Keasling, J. D. Nature 2006, 440, 940-943 10.1038/nature04640
23. Ruzicka, L. Experientia 1953, 9, 357-367 10.1007/BF02167631
24. Tantillo, D. J. Nat. Prod. Rep. 2011, 28, 1035-1053 10.1039/c1np00006c