Modeling linear and cyclic PKS intermediates through atom replacement

Journal of the American Chemical Society

Volumn 136, Issue 48, 2014, Pages 16792-16799

  Shakya, Gaurav ^a   Rivera, Heriberto ^b   Lee, D John ^b   Jaremko, Matt J ^b   La Clair, James J ^b   Fox, Daniel T ^b   Haushalter, Robert W ^b   Schaub, Andrew J ^a   Bruegger, Joel ^a   Barajas, Jesus F ^a   White, Alexander R ^a   Kaur, Parminder ^a   Gwozdziowski, Emily R ^b   Wong, Fiona ^a   Tsai, Shiou Chuan ^a   Burkart, Michael D ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASSOCIATION REACTIONS; ATOMS; KETONES; PROTEINS;

ACYL CARRIER PROTEINS; ATOM REPLACEMENT; CONVENTIONAL METHODS; NASCENT CHAINS; POLYKETIDE SYNTHASES; RESIDENCE TIME; SUBSTRATE INTERACTION; TRANSIENT INTERMEDIATE;

SUBSTRATES;

ACTINORHODINE; ACYL CARRIER PROTEIN; PEPTIDOMIMETIC AGENT; POLYKETIDE; POLYKETIDE SYNTHASE; KETONE;

ARTICLE; ATOM; BINDING AFFINITY; CYCLIZATION; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; PROTEIN BINDING; PROTEIN INTERACTION; PROTEIN PROCESSING; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; METABOLISM;

KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; POLYKETIDE SYNTHASES;

EID: 84915822600     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5064857     Document Type: Article

References (48)

1. Sadler, P. A.; Eschenmoser, A.; Scheinz, H.; Stork, G. Helv. Chem. Acta 1957, 40, 2191
2. Stork, G.; Burgstahler, A. W. J. Am. Chem. Soc. 1955, 77, 5068
3. Ruzicka, L.; Eschenmoser, A.; Heusser, H. Experientia 1953, 9, 357
4. Ruzicka, L. Experientia 1954, 50, 1
5. Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189
6. Johnson, W. S.; Semmelhack, M. F.; Sultanbawa, M. U.; Dolak, L. A. J. Am. Chem. Soc. 1968, 90, 2994
7. Schmidt, R.; Huesmann, P. L.; Johnson, W. S. J. Am. Chem. Soc. 1980, 102, 5122
8. Pichersky, E.; Noel, J. P.; Dudareva, N. Science 2006, 311, 808
9. Yoder, R. A.; Johnston, J. N. Chem. Rev. 2005, 105, 4730
10. Poralla, K. Chem. Biol. 2004, 11, 12
11. Xu, R.; Fazio, G. C.; Matsuda, S. P. Phytochemistry 2004, 65, 261
12. Akey, D. L.; Gehret, J. J.; Khare, D.; Smith, J. L. Nat. Prod. Rep. 2012, 29, 1038
13. Crawford, J. M.; Townsend, C. A. Nat. Rev. Microbiol. 2010, 8, 870
14. Khosla, C. J. Org. Chem. 2009, 74, 6416
15. Das, A.; Khosla, C. Acc. Chem. Res. 2009, 42, 631
16. Bumpus, S. B.; Kelleher, N. L. Curr. Opin. Chem. Biol. 2008, 12, 475
17. Korman, T. P.; Hill, J. A.; Vu, T. N.; Tsai, S. C. Biochemistry 2004, 43, 14529
18. Rudd, B. A.; Hopwood, D. A. J. Gen. Microbiol. 1979, 114, 35
19. Fernández-Moreno, M. A.; Martínez, E.; Caballero, J. L.; Ichinose, K.; Hopwood, D. A.; Malpartida, F. J. Biol. Chem. 1994, 269, 24854
20. Crump, M. P.; Crosby, J.; Dempsey, C. E.; Parkinson, J. A.; Murray, M.; Hopwood, D. A.; Simpson, T. J. Biochemistry 1997, 36, 6000
21. Revill, W. P.; Bibb, M. J.; Hopwood, D. A. J. Bacteriol. 1996, 178, 5660
22. Teufel, R.; Miyanaga, A.; Michaudel, Q.; Stull, F.; Louie, G.; Noel, J. P.; Baran, P. S.; Palfey, B.; Moore, B. S. Nature 2013, 503, 552
23. Ames, B. D.; Lee, M. Y.; Moody, C.; Zhang, W.; Tang, Y.; Tsai, S. C. Biochemistry 2011, 50, 8392
24. Tsai, S. C.; Lu, H.; Cane, D. E.; Khosla, C.; Stroud, R. M. Biochemistry 2002, 41, 12598
25. Pan, H.; Tsai, S. C.; Meadows, E. S.; Miercke, L. J.; Keatinge-Clay, A. T.; O'Connell, J.; Khosla, C.; Stroud, R. M. Structure 2002, 10, 1559
26. Fouché, M.; Rooney, L.; Barrett, A. G. M. J. Org. Chem. 2012, 77, 3060
27. Calo, F.; Richardson, J.; Barrett, A. G. M. Org. Lett. 2009, 11, 4910
28. Navarro, I.; Basset, J. F.; Hebbe, S.; Major, S. M.; Werner, T.; Howsham, C.; Bräckow, J.; Barrett, A. G. M. J. Am. Chem. Soc. 2008, 130, 10293
29. Harris, T. M.; Murray, T. P.; Harris, C. M.; Gumulka, M. J. Chem. Soc. Chem. Comm. 1974, 10, 362
30. Harris, T. M.; Harris, C. M. Tetrahedron 1977, 33, 2159
31. Worthington, A. S.; Burkart, M. D. Org. Biomol. Chem. 2006, 4, 44
32. Kosa, N. M.; Haushalter, R. W.; Smith, A. R.; Burkart, M. D. Nat. Methods 2012, 9, 981
33. La Clair, J. J.; Foley, T. L.; Schegg, T. R.; Regan, C. M.; Burkart, M. D. Chem. Biol. 2004, 11, 195
34. Meier, J. L.; Burkart, M. D. Methods Enzymol. 2009, 458, 219
35. Foley, T. L.; Burkart, M. D. Curr. Opin. Chem. Biol. 2007, 11, 12
36. Haushalter, R. W.; Filipp, F. V.; Ko, K. S.; Yu, R.; Opella, S. J.; Burkart, M. D. ACS Chem. Biol. 2011, 6, 413
37. Stork, G.; Hagedorn, A. A., III J. Am. Chem. Soc. 1978, 100, 3609
38. Stork, G.; La Clair, J. J.; Spargo, P.; Nargund, R. P.; Totah, N. J. Am. Chem. Soc. 1996, 118, 5304
39. Wright, P. M.; Myers, A. G. Tetrahedron 2011, 67, 9853
40. Sun, C.; Wang, Q.; Brubaker, J. D.; Wright, P. M.; Lerner, C. D.; Noson, K.; Charest, M.; Siegel, D. R.; Wang, Y. M.; Myers, A. G. J. Am. Chem. Soc. 2008, 130, 17913
41. Charest, M. G.; Siegel, D. R.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 8292
42. Roujeinikova, A.; Simon, W. J.; Gilroy, J.; Rice, D. W.; Rafferty, J. B.; Slabas, A. R. J. Mol. Biol. 2007, 365, 135
43. Płoskoń, E.; Arthur, C. J.; Kanari, A. L.; Wattana-amorn, P.; Williams, C.; Crosby, J.; Simpson, T. J.; Willis, C. L.; Crump, M. P. Chem. Biol. 2010, 17, 776
44. Evans, S. E.; Williams, C.; Arthur, C. J.; Płoskoń, E.; Wattana-amorn, P.; Cox, R. J.; Crosby, J.; Willis, C. L.; Simpson, T. J.; Crump, M. P. J. Mol. Biol. 2009, 389, 511
45. Nguyen, C.; Haushalter, R. W.; Lee, D. J.; Markwick, P. R.; Bruegger, J.; Caldara-Festin, G.; Finzel, K.; Jackson, D. R.; Ishikawa, F.; O'Dowd, B.; McCammon, J. A.; Opella, S. J.; Tsai, S. C.; Burkart, M. D. Nature 2014, 505, 427
46. Javidpour, P.; Bruegger, J.; Srithahan, S.; Korman, T. P.; Crump, M. P.; Crosby, J.; Burkart, M. D.; Tsai, S. C. Chem. Biol. 2013, 20, 1225
47. Revill, W. P.; Bibb, M. J.; Hopwood, D. A. J. Bacteriol. 1996, 178, 5660
48. Marsini, M. A.; Pettus, T. R. R.; Wenderski, T. A. Org. Lett. 2011, 13, 118