Thioesterase domains of fungal nonreducing polyketide synthases act as decision gates during combinatorial biosynthesis

Journal of the American Chemical Society

Volumn 135, Issue 29, 2013, Pages 10783-10791

  Xu, Yuquan ^a   Zhou, Tong ^b   Zhang, Shuwei ^b,c   Xuan, Li Jiang ^c   Zhan, Jixun ^b   Molnár, István ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b Utah State University   (United States)

^c Shanghai Jiao Tong University Affiliated Sixth People s Hospital   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COMBINATORIAL BIOSYNTHESIS; CONTEXT DEPENDENT; MACRO-CYCLIZATION; POLYKETIDE SYNTHASES; PRODUCT FORMATION; RELEASE MECHANISM; SECONDARY METABOLITES; STRUCTURAL CLASS;

BIOCHEMISTRY; CHASSIS; ENZYMES; FUNGI; KETONES; METABOLITES;

BIOSYNTHESIS;

POLYKETIDE SYNTHASE; PYRONE DERIVATIVE; THIOL ESTER HYDROLASE;

ARTICLE; BIOSYNTHESIS; CHEMICAL BOND; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; CYCLIZATION; HYDROLYSIS; TRANSESTERIFICATION;

POLYKETIDE SYNTHASES; POLYKETIDES; PROTEIN STRUCTURE, TERTIARY; SACCHAROMYCES CEREVISIAE; SUBSTRATE SPECIFICITY; THIOLESTER HYDROLASES;

EID: 84880809096     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4041362     Document Type: Article

References (46)

1. Crawford, J. M.; Townsend, C. A. Nat. Rev. Microbiol. 2010, 8, 879
2. Chooi, Y. H.; Tang, Y. J. Org. Chem. 2012, 77, 9933
3. Schmidt, N.; Pautz, A.; Art, J.; Rauschkolb, P.; Jung, M.; Erkel, G.; Goldring, M. B.; Kleinert, H. Biochem. Pharmacol. 2010, 79, 722
4. Elzner, S.; Schmidt, D.; Schollmeyer, D.; Erkel, G.; Anke, T.; Kleinert, H.; Förstermann, U.; Kunz, H. ChemMedChem 2008, 3, 924
5. Santagata, S.; Xu, Y. M.; Wijeratne, E. M.; Kontnik, R.; Rooney, C.; Perley, C. C.; Kwon, H.; Clardy, J.; Kesari, S.; Whitesell, L.; Lindquist, S.; Gunatilaka, A. A. L. ACS Chem. Biol. 2012, 7, 340
6. McLellan, C. A.; Turbyville, T. J.; Wijeratne, E. M. K.; Kerschen, A.; Vierling, E.; Queitsch, C.; Whitesell, L.; Gunatilaka, A. A. L. Plant Physiol. 2007, 145, 174
7. Workman, P.; Burrows, F.; Neckers, L.; Rosen, N. Ann. N.Y. Acad. Sci. 2007, 1113, 202
8. McDonald, E.; Workman, P.; Jones, K. Curr. Top. Med. Chem. 2006, 6, 1091
9. Winssinger, N.; Fontaine, J. G.; Barluenga, S. Curr. Top. Med. Chem. 2009, 9, 1419
10. Winssinger, N.; Barluenga, S. Chem. Commun. (Camb). 2007, 2007, 22
11. Cox, R. J. Org. Biomol. Chem. 2007, 5, 2010
12. Keatinge-Clay, A. T. Nat. Prod. Rep. 2012, 29, 1050
13. Xu, Y.; Espinosa-Artiles, P.; Schubert, V.; Xu, Y. M.; Zhang, W.; Lin, M.; Gunatilaka, A. A. L.; Süssmuth, R.; Molnár, I. Appl. Environ. Microbiol. 2013, 79, 2038
14. Foulke-Abel, J.; Townsend, C. A. ChemBioChem 2012, 13, 1880
15. Crawford, J. M.; Korman, T. P.; Labonte, J. W.; Vagstad, A. L.; Hill, E. A.; Kamari-Bidkorpeh, O.; Tsai, S. C.; Townsend, C. A. Nature 2009, 461, 1139
16. Thomas, R. ChemBioChem 2001, 2, 612
17. Xu, Y.; Zhou, T.; Zhou, Z.; Su, S.; Roberts, S. A.; Montfort, W. R.; Zeng, J.; Chen, M.; Zhang, W.; Zhan, J.; Molnár, I. Proc. Natl. Acad. Sci. USA. 2013, 110, 5398
18. Wang, S.; Xu, Y.; Maine, E. A.; Wijeratne, E. M. K.; Espinosa-Artiles, P.; Gunatilaka, A. A. L.; Molnár, I. Chem. Biol. 2008, 15, 1328
19. Zhou, H.; Qiao, K.; Gao, Z.; Vederas, J. C.; Tang, Y. J. Biol. Chem. 2010, 285, 41412
20. Li, Y.; Xu, W.; Tang, Y. J. Biol. Chem. 2010, 285, 22764
21. Wijeratne, E. M. K.; Paranagama, P. A.; Gunatilaka, A. A. L. Tetrahedron 2006, 62, 8439
22. Zhan, J. Curr. Top. Med. Chem. 2009, 9, 1598
23. Zhou, H.; Zhan, J.; Watanabe, K.; Xie, X.; Tang, Y. Proc. Natl. Acad. Sci. USA. 2008, 105, 6249
24. Reeves, C. D.; Hu, Z.; Reid, R.; Kealey, J. T. Appl. Environ. Microbiol. 2008, 74, 5121
25. Kim, Y. T.; Lee, Y. R.; Jin, J.; Han, K. H.; Kim, H.; Kim, J. C.; Lee, T.; Yun, S. H.; Lee, Y. W. Mol. Microbiol. 2005, 58, 1102
26. Gaffoor, I.; Brown, D. W.; Plattner, R.; Proctor, R. H.; Qi, W.; Trail, F. Eukaryot. Cell 2005, 4, 1926
27. Zhou, H.; Gao, Z.; Qiao, K.; Wang, J.; Vederas, J. C.; Tang, Y. Nat. Chem. Biol. 2012, 8, 331
28. Crawford, J. M.; Thomas, P. M.; Scheerer, J. R.; Vagstad, A. L.; Kelleher, N. L.; Townsend, C. A. Science 2008, 320, 243
29. Wang, M.; Zhou, H.; Wirz, M.; Tang, Y.; Boddy, C. N. Biochem. 2009, 48, 6288
30. Korman, T. P.; Crawford, J. M.; Labonte, J. W.; Newman, A. G.; Wong, J.; Townsend, C. A.; Tsai, S. C. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 6246
31. Du, L.; Lou, L. Nat. Prod. Rep. 2010, 27, 255
32. Vagstad, A. L.; Hill, E. A.; Labonte, J. W.; Townsend, C. A. Chem. Biol. 2012, 19, 1525
33. Fujii, I.; Watanabe, A.; Sankawa, U.; Ebizuka, Y. Chem. Biol. 2001, 8, 189
34. Gaffoor, I.; Trail, F. Appl. Environ. Microbiol. 2006, 72, 1793
35. Beck, Z. Q.; Aldrich, C. C.; Magarvey, N. A.; Georg, G. I.; Sherman, D. H. Biochemistry 2005, 44, 13457
36. Kohli, R. M.; Walsh, C. T.; Burkart, M. D. Nature 2002, 418, 658
37. Kopp, F.; Marahiel, M. A. Curr. Opin. Biotechnol. 2007, 18, 513
38. Vagstad, A. L.; Bumpus, S. B.; Belecki, K.; Kelleher, N. L.; Townsend, C. A. J. Am. Chem. Soc. 2012, 134, 6865
39. Liu, T.; Chiang, Y. M.; Somoza, A. D.; Oakley, B. R.; Wang, C. C. J. Am. Chem. Soc. 2011, 133, 13314
40. Crawford, J. M.; Vagstad, A. L.; Ehrlich, K. C.; Townsend, C. A. Bioorg. Chem. 2008, 36, 16
41. Ma, S. M.; Li, J. W.; Choi, J. W.; Zhou, H.; Lee, K. K.; Moorthie, V. A.; Xie, X.; Kealey, J. T.; Da Silva, N. A.; Vederas, J. C.; Tang, Y. Science 2009, 326, 589
42. Newman, A. G.; Vagstad, A. L.; Belecki, K.; Scheerer, J. R.; Townsend, C. A. Chem. Commun. 2012, 48, 11772
43. Vagstad, A. L.; Newman, A. G.; Storm, P. A.; Belecki, K.; Crawford, J. M.; Townsend, C. A. Angew. Chem., Int. Ed. 2013, 52, 1718
44. Yeh, H. H.; Chang, S. L.; Chiang, Y. M.; Bruno, K. S.; Oakley, B. R.; Wu, T. K.; Wang, C. C. Org. Lett. 2013, 15, 756
45. Hong, H.; Leadlay, P. F.; Staunton, J. FEBS J. 2009, 276, 7057
46. Lee, K. K.; Da Silva, N. A.; Kealey, J. T. Anal. Biochem. 2009, 394, 75