Substrate controlled divergence in polyketide synthase catalysis

Journal of the American Chemical Society

Volumn 137, Issue 11, 2015, Pages 3735-3738

  Hansen, Douglas A ^a   Koch, Aaron A ^a   Sherman, David H ^a,b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ESTERIFICATION; ESTERS; KETONES; PLANTS (BOTANY);

BIOCHEMICAL CHARACTERIZATION; CATALYTIC CYCLES; FUNCTIONALIZED; MULTIPLE DOMAINS; POLYKETIDE SYNTHASES; PRODUCT FORMATION; SUBSTRATE ENGINEERING; SYNTHETIC SUBSTRATES;

SUBSTRATES;

HYDROXYL GROUP; PIKROMYCIN; POLYKETIDE SYNTHASE; MACROLIDE; POLYKETIDE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CYCLIZATION; DIASTEREOISOMER; ELECTROPHILICITY; IN VITRO STUDY; MACROLACTONIZATION; OXIDATION; REACTION TIME; STREPTOMYCES VENEZUELAE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; GENETICS; METABOLISM;

MACROLIDES; MOLECULAR STRUCTURE; POLYKETIDE SYNTHASES; POLYKETIDES; SUBSTRATE SPECIFICITY;

EID: 84925834950     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja511743n     Document Type: Article

References (26)

1. Fischbach, M. A.; Walsh, C. T. Chem. Rev. 2006, 106, 3468
2. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2012, 75, 311
3. Tsai, S.-C.; Lu, H.; Cane, D. E.; Khosla, C.; Stroud, R. M. Biochemistry 2002, 41, 12598
4. Kittendorf, J. D.; Beck, B. J.; Buchholz, T. J.; Seufert, W.; Sherman, D. H. Chem. Biol. 2007, 14, 944
5. Cane, D. E.; Yang, C. C. J. Am. Chem. Soc. 1987, 109, 1255
6. Yue, S.; Duncan, J. S.; Yamamoto, Y.; Hutchinson, C. R. J. Am. Chem. Soc. 1987, 109, 1253
7. Tosin, M.; Betancor, L.; Stephens, E.; Li, W. M.; Spencer, J. B.; Leadlay, P. F. ChemBioChem 2010, 11, 539
8. Spiteller, D.; Waterman, C. L.; Spencer, J. B. Angew. Chem., Int. Ed. 2005, 44, 7079
9. Wu, J.; He, W.; Khosla, C.; Cane, D. E. Angew. Chem., Int. Ed. 2005, 44, 7557
10. Aldrich, C. C.; Beck, B. J.; Fecik, R. A.; Sherman, D. H. J. Am. Chem. Soc. 2005, 127, 8441
11. Aldrich (ref 7) monitored 10-dml (2) formation using Pik pentaketide (3) with PikAIII-TE and PikAIII/PikAIV constructs, but not with Pik hexaketide (4) and PikAIV due to limitations of the assay employed.
12. Yin, Y.; Lu, H.; Khosla, C.; Cane, D. E. J. Am. Chem. Soc. 2003, 125, 5671
13. Hansen, D. A.; Rath, C. M.; Eisman, E. B.; Narayan, A. R.; Kittendorf, J. D.; Mortison, J. D.; Yoon, Y. J.; Sherman, D. H. J. Am. Chem. Soc. 2013, 135, 11232
14. Aldrich, C. C.; Venkatraman, L.; Sherman, D. H.; Fecik, R. A. J. Am. Chem. Soc. 2005, 127, 8910
15. Mortison, J. D.; Kittendorf, J. D.; Sherman, D. H. J. Am. Chem. Soc. 2009, 131, 15784
16. Harris, T. M.; Harris, C. M. Tetrahedron 1977, 33, 2159
17. Crosby, J.; Crump, M. P. Nat. Prod. Rep. 2012, 29, 1111
18. Whicher, J. R.; Dutta, S.; Hansen, D. A.; Hale, W. A.; Chemler, J. A.; Dosey, A. M.; Narayan, A. R. H.; Hakansson, K.; Sherman, D. H.; Smith, J. L.; Skiniotis, G. Nature 2014, 510, 560
19. Schwartz, M. E.; Breaker, R. R.; Asteriadis, G. T.; deBear, J. S.; Gough, G. R. Bioorg. Med. Chem. Lett. 1992, 2, 1019
20. Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. Tetrahedron Lett. 1994, 35, 7171
21. Sawada, D.; Ito, Y. Tetrahedron Lett. 2001, 42, 2501
22. Epp, J. B.; Widlanski, T. S. J. Org. Chem. 1998, 64, 29
23. Pohl, N. L.; Gokhale, R. S.; Cane, D. E.; Khosla, C. J. Am. Chem. Soc. 1998, 120, 11206
24. Broadhurst, R. W.; Nietlispach, D.; Wheatcroft, M. P.; Leadlay, P. F.; Weissman, K. J. Chem. Biol. 2003, 10, 723
25. Gokhale, R. S.; Hunziker, D.; Cane, D. E.; Khosla, C. Chem. Biol. 1999, 6, 117
26. Aggarwal, R.; Caffrey, P.; Leadlay, P. F.; Smith, C. J.; Staunton, J. J. Chem. Soc., Chem. Commun. 1995, 15, 1519