Elucidating the cyclization cascades in xiamycin biosynthesis by substrate synthesis and enzyme characterizations

Organic Letters

Volumn 17, Issue 2, 2015, Pages 306-309

  Li, Huixian ^a   Sun, Yu ^b   Zhang, Qingbo ^a   Zhu, Yiguang ^a   Li, Shu Ming ^c   Li, Ang ^b   Zhang, Changsheng ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3-(EPOXYFARNESYL)-INDOLE; 3-FARNESYLINDOLE; ENZYME PRECURSOR; EPOXIDE; INDOLE; INDOLE DERIVATIVE; MEMBRANE PROTEIN; OXIDOREDUCTASE; SESQUITERPENE; TERPENE; XIAMYCIN;

BIOCATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METABOLISM; OXIDATION REDUCTION REACTION; SYNTHESIS;

BIOCATALYSIS; CYCLIZATION; ENZYME PRECURSORS; EPOXY COMPOUNDS; INDOLES; MEMBRANE PROTEINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXIDOREDUCTASES; SESQUITERPENES; TERPENES;

EID: 84921263865     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503399b     Document Type: Article

References (23)

1. Marcos, I. S.; Moro, R. F.; Costales, I.; Basabe, P.; Diez, D. Nat. Prod. Rep. 2013, 30, 1509-1526
2. Li, S. M. Nat. Prod. Rep. 2010, 27, 57-78
3. Takada, K.; Kajiwara, H.; Imamura, N. J. Nat. Prod. 2010, 73, 698-701
4. Ding, L.; Munch, J.; Goerls, H.; Maier, A.; Fiebig, H. H.; Lin, W. H.; Hertweck, C. Bioorg. Med. Chem. Lett. 2010, 20, 6685-6687
5. Ding, L.; Maier, A.; Fiebig, H. H.; Lin, W. H.; Hertweck, C. Org. Biomol. Chem. 2011, 9, 4029-4031
6. Zhang, Q.; Mándi, A.; Li, S.; Chen, Y.; Zhang, W.; Tian, X.; Zhang, H.; Li, H.; Zhang, W.; Zhang, S.; Ju, J.; Kurtán, T.; Zhang, C. Eur. J. Org. Chem. 2012, 2012, 5256-5262
7. Xu, W.; Gavia, D. J.; Tang, Y. Nat. Prod. Rep. 2014, 31, 1474-1487
8. Rosen, B. R.; Werner, E. W.; OBrien, A. G.; Baran, P. S. J. Am. Chem. Soc. 2014, 136, 5571-5574
9. Sun, Y.; Chen, P.; Zhang, D.; Baunach, M.; Hertweck, C.; Li, A. Angew. Chem., Int. Ed. 2014, 53, 9012-9016
10. Meng, Z.; Yu, H.; Li, L.; Tao, W.; Chen, H.; Wan, M.; Yang, P.; Edmonds, D. J.; Zhong, J.; Li, A. Nat. Comm. DOI: 10.1038/ncomms7096.
11. Li, H.; Zhang, Q.; Li, S.; Zhu, Y.; Zhang, G.; Zhang, H.; Tian, X.; Zhang, S.; Ju, J.; Zhang, C. J. Am. Chem. Soc. 2012, 134, 8996-9005
12. Xu, Z.; Baunach, M.; Ding, L.; Hertweck, C. Angew. Chem., Int. Ed. 2012, 51, 10293-10297
13. Zhang, Q.; Li, H.; Li, S.; Zhu, Y.; Zhang, G.; Zhang, H.; Zhang, W.; Shi, R.; Zhang, C. Org. Lett. 2012, 14, 6142-6145
14. Baunach, M.; Ding, L.; Bruhn, T.; Bringmann, G.; Hertweck, C. Angew. Chem., Int. Ed. 2013, 52, 9040-9043
15. Itoh, T.; Tokunaga, K.; Matsuda, Y.; Fujii, I.; Abe, I.; Ebizuka, Y.; Kushiro, T. Nat. Chem. 2010, 2, 858-864
16. Tagami, K.; Liu, C.; Minami, A.; Noike, M.; Isaka, T.; Fueki, S.; Shichijo, Y.; Toshima, H.; Gomi, K.; Dairi, T.; Oikawa, H. J. Am. Chem. Soc. 2013, 135, 1260-1263
17. See also an excellent review: Baunach, M.; Franke, J.; Hertweck, C. Angew. Chem., Int. Ed. 2014, 10.1002/anie.201407883
18. Kolb, H. C.; Vannieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547
19. Lin, A. J.; Yang, J.; Hashim, M. Org. Lett. 2013, 15, 1950-1953
20. Munyemana, F.; Frisquehesbain, A. M.; Devos, A.; Ghosez, L. Tetrahedron Lett. 1989, 30, 3077-3080
21. Zhou, H.; Wang, Y.; Yu, Y.; Bai, T.; Chen, L.; Liu, P.; Guo, H.; Zhu, C.; Tao, M.; Deng, Z. Curr. Microbiol. 2012, 64, 185-190
22. Oliynyk, M.; Stark, C. B. W.; Bhatt, A.; Jones, M. A.; Hughes-Thomas, Z. A.; Wilkinson, C.; Oliynyk, Z.; Demydchuk, Y.; Staunton, J.; Leadlay, P. F. Mol. Microbiol. 2003, 49, 1179-1190
23. Migita, A.; Watanabe, M.; Hirose, Y.; Watanabe, K.; Tokiwano, T.; Kinashi, H.; Oikawa, H. Biosci. Biotechnol. Biochem. 2009, 73, 169-176