Timing of the Δ10,12-Δ11,13double bond migration during ansamitocin biosynthesis in actinosvnnema pretiosum

Journal of the American Chemical Society

Volumn 131, Issue 11, 2009, Pages 3812-3813

  Taft, Florian ^a   Brunjes, Marco ^a   Knobloch, Tobias ^a   Floss, Heinz G ^b   Kirschning, Andreas ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOUBLE BOND MIGRATION; DOUBLE BONDS; OPTICALLY ACTIVE; POLYKETIDE; THIOESTER; THIOESTERS;

BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; TIME MEASUREMENT;

BIOSYNTHESIS;

ANSAMITOCIN; ANTINEOPLASTIC AGENT; PLANT EXTRACT; POLYKETIDE; ALKENE; ANTIINFECTIVE AGENT; MAYTANSINE; TUBULIN MODULATOR;

ACTINOSYNNEMA PRETIOSUM; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOSYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEHYDRATION; ENANTIOMER; MEDICINAL PLANT; MUTANT; NONHUMAN; STEREOCHEMISTRY; ACTINOMYCETALES; ANALOGS AND DERIVATIVES; METABOLISM;

ACTINOMYCETALES; ALKENES; ANTI-BACTERIAL AGENTS; CHEMICAL PROCESSES; MAYTANSINE; TUBULIN MODULATORS;

EID: 67849110452     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8088923     Document Type: Article

References (23)

1. Kupchan, S. M.; Komoda, Y.; Court, W. A.; Thomas, G. J.; Smith, R. M.; Karim, A.; Gilmore, C. J.; Haltiwanger, R. C.; Bryan, R. F. J. Am. Chem. Soc. 1972, 94, 1354-1356.
2. Higashide, E.; Asai, M.; Ootsu, K.; Tanida, S.; Kozai, Y.; Hasegawa, T.; Kishi, T.; Sugino, Y.; Yoneda, M. Nature 1977, 270, 721-722.
3. Review Cassady, J. M.; Chan, K. K.; Floss, H. G.; Leistner, E. Chem. Pharm. Bull. 2004, 52, 1-26.
4. Hatano, K.; Akiyama, S.-L; Asai, M.; Rickards, R. W. J. Antibiot. 1982, 35, 1415-1417.
5. Yu, T.-W.; Bai, L.; Clade, D.; Hoffmann, D.; Toelzer, S.; Trinh, K. Q.; Xu, J.; Moss, S. J.; Leistner, E.; Floss, H. G. Proc. Nat. Acad. Sci. U.S.A. 2002, 99, 7968-7973.
6. Spiteller, P.; Bai, L.; Shang, G.; Carroll, B. J.; Yu, T.-W.; Floss, H. G. J. Am. Chem. Soc. 2003, 125, 14236-14237.
7. Kubota, T.; Brunjes, M.; Frenzel, T.; Xu, J.; Kirschning, A.; Floss, H. G. ChemBioChem 2006, 7, 1221-1225.
8. (a) Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
9. (b) Andrus, M. B.; Meredith, E. L.; Somar Sekhar, B. B. V. Org. Lett. 2001, 3, 259-262.
10. Gilbert, I. H.; Ginty, M.; O'Neill, J. A.; Simpson, T. J.; Staunton, J. Bioorg. Med. Chem. Lett. 1995, 5, 1587-1590.
11. 13C NMR) after purification by flash column chromatography.
12. Frenzel, T.; Brunjes, M.; Quitschalle, M.; Kirschning, A. Org. Lett. 2006, 8, 135-138.
13. Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702-12703.
14. See Supporting Information.
15. Wu, J.; Zaleski, T. J.; Valenzano, C.; Khosla, C.; Cane, D. E. J. Am. Chem. Soc. 2005, 127, 17393-17404.
16. Smith, S.; Tsai, S.-C. Nat. Prod. Rep. 2007, 24, 1041-1072.
17. 18 inversion of configuration in KS-catalyzed Claisen condensations. Therefore, an epimerization must take place at this center at some stage in the biosynthesis prior to loading onto KS4.
18. Dorrestein, P. C.; Van Lanen, S. G.; Li, W.; Zhao, C.; Deng, Z.; Shen, B.; Kelleher, N. L. J. Am. Chem. Soc. 2006, 128, 10386-10387.
19. Weissman, K. J.; Timoney, M.; Bycroft, M.; Grice, P.; Hanefeld, U.; Staunton, J.; Leadlay, P. F. Biochemistry 1997, 36, 13849-18855.
20. (a) Caffrey, P. Chem. Biol. 2003, 10, 1060-1062.
21. (b) Reid, R.; Piagentini, M.; Rodriguez, E.; Ashley, G.; Viswanathan, N.; Carney, J.; Santi, D. V.; Hutchinson, R.; McDaniel, R. Biochemistry 2003, 42, 72-79.
22. Castonguay, R.; Valenzo, C. R.; Chen, A. Y.; Keatinge-Clay, A.; Khosla, C.; Cane, D. E. J. Am. Chem. Soc. 2008, 130, 11598-11599.
23. Carrol, B. J.; Moss, S. J.; Bai, L.; Kato, Y.; Toelzer, S.; Yu, T.-W.; Floss, H. G. J. Am. Chem. Soc. 2002, 124, 4176-4177.