Biochemical and structural characterization of germicidin synthase: Analysis of a type III polyketide synthase that employs Acyl-ACP as a starter unit donor

Journal of the American Chemical Society

Volumn 134, Issue 17, 2012, Pages 7359-7366

  Chemler, Joseph A ^a   Buchholz, Tonia J ^a   Geders, Todd W ^a   Akey, David L ^a,c,d   Rath, Christopher M ^a   Chlipala, George E ^a   Smith, Janet L ^a,b   Sherman, David H ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^c PURDUE UNIVERSITY   (United States)

^d R and D Systems Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; ACYL CARRIER PROTEINS; ACYL GROUP; ACYL-ACP; ACYL-COA; ARGININE RESIDUE; CARRIER PROTEINS; CATALYTIC EFFICIENCIES; COENZYME A; ENGINEERED SYSTEMS; FATTY ACID BIOSYNTHESIS; HELICAL BUNDLE; IN-VITRO; KINETIC PROPERTIES; POLYKETIDES; STREPTOMYCES COELICOLOR; STRUCTURAL CHARACTERIZATION; SYNTHASES; THIOESTERS; TYPE III POLYKETIDE SYNTHASE;

AMINO ACIDS; BIOCHEMISTRY; CRYSTAL STRUCTURE; SUBSTRATES;

STARTERS;

ACYL CARRIER PROTEIN; ACYL COENZYME A; ARGININE; GERMICIDIN SYNTHASE; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME KINETICS; ENZYME RECONSTITUTION; ENZYME STRUCTURE; ENZYME SYNTHESIS; FATTY ACID SYNTHESIS; IN VITRO STUDY; NONHUMAN; PROTEIN PROTEIN INTERACTION; STREPTOMYCES COELICOLOR;

ACYL CARRIER PROTEIN; ACYL COENZYME A; BACTERIAL PROTEINS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MUTATION; POLYKETIDE SYNTHASES; PROTEIN BINDING; PYRONES; SIGNAL TRANSDUCTION; STREPTOMYCES COELICOLOR; SUBSTRATE SPECIFICITY;

EID: 84860810079     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2112228     Document Type: Article

References (62)

1. Austin, M. B.; Noel, A. J. P. Nat. Prod. Rep. 2003, 20, 79
2. Walsh, C. T. Science 2004, 303, 1805
3. Abe, I.; Morita, H. Nat. Prod. Rep. 2010, 27, 809
4. Saruwatari, T.; Praseuth, A. P.; Sato, M.; Torikai, K.; Noguchi, H.; Watanabe, K. J. Antibiot. 2011, 64, 9
5. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2007, 70, 461
6. Hill, A. M. Nat. Prod. Rep. 2006, 23, 256
7. Staunton, J.; Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380
8. Fischbach, M. A.; Walsh, C. T. Chem. Rev. 2006, 106, 3468
9. Hertweck, C.; Luzhetskyy, A.; Rebets, Y.; Bechthold, A. Nat. Prod. Rep. 2007, 24, 162
10. Hertweck, C. Angew. Chem., Int. Ed. 2009, 48, 4688
11. Walsh, C. T. Chembiochem 2002, 3, 125
12. Olano, C.; Mendez, C.; Salas, J. A. Microbial Biotech. 2011, 4, 144
13. Xue, Q.; Ashley, G.; Hutchinson, C. R.; Santi, D. V. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 11740
14. Abe, I.; Morita, H.; Nomura, A.; Noguchi, H. J. Am. Chem. Soc. 2000, 122, 11242
15. Morita, H.; Noguchi, H.; Schroder, J.; Abe, I. Eur. J. Biochem. 2001, 268, 3759
16. Morita, H.; Yamashita, M.; Shi, S. P.; Wakimoto, T.; Kondo, S.; Kato, R.; Sugio, S.; Kohno, T.; Abe, I. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 13504
17. Chemler, J. A.; Yan, Y. J.; Leonard, E.; Koffas, M. A. G. Org. Lett. 2007, 9, 1855
18. Werner, S. R.; Chen, H.; Jiang, H. X.; Morgan, J. A. J. Mol. Catal. B: Enzym. 2010, 66, 257
19. Katsuyama, Y.; Funa, N.; Miyahisa, I.; Horinouchi, S. Chem. Biol. 2007, 14, 613
20. Abe, I.; Watanabe, T.; Morita, H.; Kohno, T.; Noguchi, H. Org. Lett. 2006, 8, 499
21. Shi, S. P.; Wanibuchi, K.; Morita, H.; Endo, K.; Noguchi, H.; Abe, I. Org. Lett. 2009, 11, 551
22. Gruschow, S.; Buchholz, T. J.; Seufert, W.; Dordick, J. S.; Sherman, D. H. Chembiochem 2007, 8, 863
23. Miyanaga, A.; Funa, N.; Awakawa, T.; Horinouchi, S. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 871
24. Nakano, C.; Ozawa, H.; Akanuma, G.; Funa, N.; Horinouchi, S. J. Bacteriol. 2009, 191, 4916
25. Hayashi, T.; Kitamura, Y.; Funa, N.; Ohnishi, Y.; Horinouchi, S. Chembiochem 2011, 12, 2166
26. Austin, M. B.; Saito, T.; Bowman, M. E.; Haydock, S.; Kato, A.; Moore, B. S.; Kay, R. R.; Noel, J. P. Nat. Chem. Biol. 2006, 2, 494
27. Song, L. J.; Barona-Gomez, F.; Corre, C.; Xiang, L. K.; Udwary, D. W.; Austin, M. B.; Noel, J. P.; Moore, B. S.; Challis, G. L. J. Am. Chem. Soc. 2006, 128, 14754
28. Aoki, Y.; Matsumoto, D.; Kawaide, H.; Natsume, M. J. Antibiot. 2011, 64, 607
29. Han, L.; Lobo, S.; Reynolds, K. A. J. Bacteriol. 1998, 180, 4481
30. Petersen, F.; Zahner, H.; Metzger, J. W.; Freund, S.; Hummel, R. P. J. Antibiot. 1993, 46, 1126
31. Sugiyama, Y.; Oya, A.; Kudo, T.; Hirota, A. J. Antibiot. 2010, 63, 365
32. Taoka, S.; Padmakumar, R.; Lai, M. T.; Liu, H. W.; Banerjee, R. J. Biol. Chem. 1994, 269, 31630
33. Kappe, T.; Aigner, R.; Roschger, P.; Schnell, B.; Stadlbauer, W. Tetrahedron 1995, 51, 12923
34. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307
35. Long, F.; Vagin, A. A.; Young, P.; Murshudov, G. N. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2008, 64, 125
36. Austin, M. B.; Izumikawa, M.; Bowman, M. E.; Udwary, D. W.; Ferrer, J. L.; Moore, B. S.; Noel, J. P. J. Biol. Chem. 2004, 279, 45162
37. Storoni, L. C.; McCoy, A. J.; Read, R. J. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 432
38. McCoy, A. J.; Grosse-Kunstleve, R. W.; Storoni, L. C.; Read, R. J. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2005, 61, 458
39. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallogr., Sect. D: Biol. Crystallogr. 1997, 53, 240
40. Emsley, P.; Cowtan, K. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2126
41. Adams, P. D.; Grosse-Kunstleve, R. W.; Hung, L. W.; Ioerger, T. R.; McCoy, A. J.; Moriarty, N. W.; Read, R. J.; Sacchettini, J. C.; Sauter, N. K.; Terwilliger, T. C. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2002, 58, 1948
42. Painter, J.; Merritt, E. A. J. Appl. Crystallogr. 2006, 39, 109
43. Quadri, L. E. N.; Weinreb, P. H.; Lei, M.; Nakano, M. M.; Zuber, P.; Walsh, C. T. Biochem. J. 1998, 37, 1585
44. Sanchez, C.; Du, L. C.; Edwards, D. J.; Toney, M. D.; Shen, B. Chem. Biol. 2001, 8, 725
45. Li, Y. L.; Florova, G.; Reynolds, K. A. J. Bacteriol. 2005, 187, 3795
46. Zhang, Y. M.; Rao, M. S.; Heath, R. J.; Price, A. C.; Olson, A. J.; Rock, C. O.; White, S. W. J. Biol. Chem. 2001, 276, 8231
47. Okamura, E.; Tomita, T.; Sawa, R.; Nishiyama, M.; Kuzuyama, T. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 11265
48. Funa, N.; Ohnishi, Y.; Ebizuka, Y.; Horinouchi, S. J. Biol. Chem. 2002, 277, 4628
49. Zhao, H. M.; Zha, W. J.; Rubin-Pitel, S. B. J. Biol. Chem. 2006, 281, 32036
50. Chen, H. W.; Tseng, C. C.; Hubbard, B. K.; Walsh, C. T. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 14901
51. Funabashi, M.; Funa, N.; Horinouchi, S. J. Biol. Chem. 2008, 283, 13983
52. Funa, N.; Ozawa, H.; Hirata, A.; Horinouchi, S. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 6356
53. He, X.; Reynolds, K. A. Antimicrob. Agents Chemother. 2002, 46, 1310
54. Piel, J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 14002
55. Zhang, Y. M.; Wu, B. N.; Zheng, J.; Rock, C. O. J. Biol. Chem. 2003, 278, 52935
56. Parris, K. D.; Lin, L.; Tam, A.; Mathew, R.; Hixon, J.; Stahl, M.; Fritz, C. C.; Seehra, J.; Somers, W. S. Structure 2000, 8, 883
57. Rafi, S.; Novichenok, P.; Kolappan, S.; Zhang, X. J.; Stratton, C. F.; Rawat, R.; Kisker, C.; Simmerling, C.; Tonge, P. J. J. Biol. Chem. 2006, 281, 39285
58. Arthur, C. J.; Williams, C.; Pottage, K.; Ploskon, E.; Findlow, S. C.; Burston, S. G.; Simpson, T. J.; Crump, M. P.; Crosby, J. ACS Chem. Biol. 2009, 4, 625
59. Concepcion, J. Comb. Chem. High Throughput Screening 2009, 12, 791
60. Qiu, X.; Janson, C. A.; Smith, W. W.; Head, M.; Lonsdale, J.; Konstantinidis, A. K. J. Mol. Biol. 2001, 307, 341
61. Alhamadsheh, M. M.; Musayev, F.; Komissarov, A. A.; Sachdeva, S.; Wright, H. T.; Scarsdale, N.; Florova, G.; Reynolds, K. A. Chem. Biol. 2007, 14, 513
62. Davis, I. W.; Murray, L. W.; Richardson, J. S.; Richardson, D. C. Nucleic Acids Res. 2004, 32, W615