Synthetic chain terminators off-load intermediates from a type I polyketide synthase

ChemBioChem

Volumn 11, Issue 4, 2010, Pages 539-546

  Tosin, Manuela ^a   Betancor, Lorena ^a,b   Stephens, Elaine ^a,c   Li, W M Ariel ^a   Spencer, Jonathan B ^a   Leadlay, Peter F ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b IMDEA FOOD INSTITUTE   (Spain)

^c MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

Author keywords

Biosynthesis; DEBS3; Methylmalonyl analogues; Polyketides; Trapped intermediates

Indexed keywords

6 DEOXYERYTHRONOLIDE B SYNTHASE 3; CYSTEAMINE DERIVATIVE; PANTETHEINE; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CATALYSIS; ENZYME ANALYSIS; ENZYME SUBSTRATE; ENZYME SYNTHESIS; ESCHERICHIA COLI; GENETIC ENGINEERING; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; STREPTOMYCES COELICOLOR;

CYSTEAMINE; MACROLIDES; MALONATES; MOLECULAR STRUCTURE; PANTETHEINE; POLYKETIDE SYNTHASES; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY;

EID: 77149154347     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900772     Document Type: Article

References (49)

1. a) J. Staunton, K. J. Weissman, Nat. Prod. Rep. 2001, 18, 380-416;
2. b) B. J. Rawlings, Nat. Prod. Rep. 2001, 18, 231-281;
3. c) L. Katz, Methods Enzymol. 2009, 459, 113-142.
4. J. Cortes, S. F. Haydock, G. A. Roberts, D. J. Bevitt, P. F. Leadlay, Nature 1990, 348, 176-178.
5. T. Schupp, C. Toupet, N. Engel, S. Goff, FEMS Microbiol. Lett. 1998, 159, 201-207.
6. L. Neckers, T. W. Schulte, E. Mimnaugh, Invest. New Drugs 1999, 17, 361-373.
7. H. Ikeda, T. Nonomiya, M. Usami, T. Ohta, S. Omura, Proc Natl. Acad. Sci. USA 1999, 96, 9509-9514.
8. K. M. Abu-Salah, Br. J. Biomed. Sci. 1996, 53, 122-133.
9. S. Gaisser, C. J. Martin, B. Wilkinson, R. M. Sheridan, R. E. Lill, A. J. Weston, S. J. Ready, C. Waldron, G. D. Crouse, P. F. Leadlay, J. Staunton, Chem. Commun. 2002, 618-619.
10. M. A. Gregory, H. Hong, R. E. Lill, S. Gaisser, H. Petkovic, L. Low, L. S. Sheehan, I. Carletti, S. J. Ready, M. J. Ward, A. L. Kaja, A. J. Weston, I. R. Challis, P. F. Leadlay, C. J. Martin, B. Wilkinson, R. M. Sheridan, Org. Biomol. Chem. 2006, 4, 3565-3568.
11. a) K. J. Weissman, P. F. Leadlay, Nat. Rev. Microbiol. 2005, 3, 925-936;
12. b) S. G. Van Lanen, B. Shen, Curr. Opin. Drug Discov. Devel. 2008, 11, 186- 195.
13. J. W.-H. Li, J. C. Vederas, Science 2009, 325, 161-165.
14. C. Khosla, S. Kapur, D. E. Cane, Curr. Opin. Chem. Biol. 2009, 13, 135 1439.
15. a) C. Corre, G. Challis, Nat. Prod. Rep. 2009, 26, 977-986;
16. b) H. Gross, Curr. Opin. Drug Discov. Devel. 2009, 12, 207-219.
17. S. J. Moss, C. J. Martin, B. Wilkinson, Nat. Prod. Rep. 2004, 21, 575-593.
18. C. Hertweck, Angew. Chem. 2009, 121, 4782-4811;
19. Angew. Chem. Int. Ed. 2009, 48, 4688-4716.
20. a) J. Cort́s, K. E. H. Wiesmann, G. A. Roberts, M. J. B. Brown, J. Staunton, P. F. Leadlay, Science 1995, 268, 1487-1489;
21. b) J. Zhang, S. G. Van Lanen, J. Ju, W. Liu, P. C. Dorrestein, W. Li, N. L. Kelleher, B. Shen, Proc. Natl. Acad. Sci. USA 2008, 105, 1460-1465.
22. a) T. W. Yu, Y. M. Shen, Y. Doi-Katayama, L. Tang, C. Park, B. S. Moore, C. R. Hutchinson, H. G. Floss, Proc. Natl. Acad. Sci. USA 1999, 96, 9051-9056;
23. b) J. Moldenhauer, X.-H. Chen, R. Borriss, J. Piel, Angew. Chem. 2007, 119, 8343-8345;
24. Angew. Chem. Int. Ed. 2007, 46, 8195-8197;
25. c) B. Kusebauch, B. Busch, K. Scherlach, M. Roth, C. Hertweck, Angew. Chem. Int. Ed. 2009, 121, 5101-5104.
26. R. Castonguay, W. He, A. Y. Chen, C. Khosla, D. E. Cane, J. Am. Chem. Soc. 2007, 129, 13758-13769.
27. P. C. Dorrestein, N. L. Kelleher, Nat. Prod. Rep. 2006, 23, 893-918.
28. a) S. B. Bumpus, B. S. Evans, P. M. Thomas, I. Ntai, N. L. Kelleher, Nat. Biotechnol. 2009, 27, 951-956;
29. b) S. B. Bumpus, N. L. Kelleher, Curr. Opin. Chem. Biol. 2008, 12, 475-482.
30. a) H. Hong, A. N. Appleyard, A. P. Siskos, J. Garcia-Bernardo, J. Staunton, P. F. Leadlay, FEBS J. 2005, 272, 2373-2387;
31. b) H. Hong, P. F. Leadlay, J. Staunton, FEBS J. 2009, 276, 7057-7069.
32. a) S. Smith, S.-C. Tsai, Nat. Prod. Rep. 2007, 24, 1041-1072;
33. b) T. Maier, M. Leibundgut, N. Ban, Science 2008, 321, 1315-1322.
34. M. Tosin, D. Spiteller, J. B. Spencer, ChemBioChem 2009, 10, 1714-1723.
35. D. Spiteller, C. L. Waterman, J. B. Spencer, Angew. Chem. 2005, 117, 7241-7244;
36. Angew. Chem. Int. Ed. 2005, 44, 7079-7082.
37. Y. A. Chan, A. M. Podevels, B. M. Kevany, M. G. Thomas, Nat. Prod. Rep. 2009, 26, 90-114.
38. K. Reuter, M. R. Mofid, M. A. Marahiel, R. Ficner, EMBO J. 1999, 18, 6823-6831.
39. F. Sanger, S. Nicklen, A. R. Coulson, Proc. Natl. Acad. Sci. USA 1977, 74, 5463-5467.
40. P. Caffrey, D. J. Bevitt, J. Staunton, P. F. Leadlay, FEBS Lett. 1992, 304, 225-228.
41. G. A. Roberts, J. Staunton, P. F. Leadlay, Eur. J. Biochem. 1993, 214, 305-311.
42. L. Betancor, M.-J. Ferńndez, K. J. Weissman, P. F. Leadlay, ChemBioChem 2008, 9, 2962-2966.
43. a) N. L. Pohl, R. S. Gokhale, D. E. Cane, C. Khosla, J. Am. Chem. Soc. 1998, 120, 11206-11207;
44. b) D. E. Cane, G. Luo, C. Koshla, C. M. Kao, L. Katz, J. Antibiot. 1995, 48, 647-651.
45. a) A. S. Worthington, H. J. Rivera, J. W. Torpey, M. D. Alexander, M. D. Burkart, ACS Chem. Biol. 2006, 1, 687-691;
46. b) G. H. Hur, J. L. Meier, J. Baskin, J. A. Codelli, C. R. Bertozzi, M. A. Marahiel, M. D. Burkart, Chem. Biol. 2009, 16, 372-381.
47. a) A. Y. Chen, N. A. Schnarr, C.-Y. Kim, D. E. Cane, C. Khosla, J. Am. Chem. Soc. 2006, 128, 3067-3074;
48. b) C.-Y. Kim, V. Y. Alekseyev, A. Y. Chen, Y. Tang, D. E. Cane, C. Khosla, Biochemistry 2004, 43, 13892-13898.
49. To the best of our knowledge 6-acetamido-3-oxohexanoic acid (20) has been previously obtained in vitro by transamination between 6-L-β-lysine and α-ketoglutarate, G. Bozler, J. M. Robertson, M. Ohsugi, C. Hensley, H. A. Barker, Arch. Biochem. Biophys. 1979, 197, 226-235.