Molecular analysis of the benastatin biosynthetic pathway and genetic engineering of altered fatty acid-polyketide hybrids

Journal of the American Chemical Society

Volumn 129, Issue 18, 2007, Pages 6022-6030

  Xu, Zhongli ^a   Schenk, Angéla ^a   Hertweck, Christian ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BENASTATIN BIOSYNTHETIC; FREDERICAMYCIN PATHWAYS; HEXACYCLIC RING SYSTEM; SYNTHASE PRIMERS;

BIOSYNTHESIS; CLONING; DERIVATIVES; ENZYME INHIBITION; GENE EXPRESSION; MOLECULAR DYNAMICS;

FATTY ACIDS;

ANTIBIOTIC AGENT; BE 43767A; BENASTATIN DERIVATIVE; FATTY ACID; FATTY ACID SYNTHASE INHIBITOR; FREDERICAMYCIN A; GRISEORHODIN; HEXANOIC ACID; POLYKETIDE; RUBROMYCIN; TAN 1532B; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CHEMICAL ANALYSIS; CLUSTER ANALYSIS; CONTROLLED STUDY; DERIVATIZATION; DRUG SYNTHESIS; GENE DELETION; GENE EXPRESSION; GENETIC ANALYSIS; GENETIC ENGINEERING; NONHUMAN; NUCLEOTIDE SEQUENCE;

BASE SEQUENCE; CLONING, MOLECULAR; DNA PRIMERS; FATTY ACIDS; GENETIC ENGINEERING; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MULTIGENE FAMILY; NAPHTHACENES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 34248586053     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja069045b     Document Type: Article

References (83)

1. Hertweck, C.; Luzhetskyy, A.; Rebets, Y.; Bechthold, A. Nat. Prod. Rep. 2007, 24, 162-190.
2. Rawlings, B. J. Nat. Prod. Rep. 1999, 16, 425-484.
3. Shen, B. Top. Curr. Chem. 2000, 209, 1-51.
4. O'Hagan, D. The Polyketide Metabolites; Ellis Horwood: Chichester, 1991.
5. Kieser, T.; Bibb, M. J.; Buttner, M. J.; Chater, K. F.; Hopwood, D. A. Practical Streptomyces Genetics: The John Innes Foundation: Norwich, U.K., 2000.
6. Pfeifer, B. A.; Khosla, C, Microbiol. Mol. Biol Rev. 2001, 65, 106-118.
7. Hopwood, D. A. Chem. Rev. 1997, 97, 2465-2497.
8. Schneider, G, Curr. Opin. Struct. Biol. 2005, 15, 629-636.
9. Keatinge-Clay, A. T.; Maltby, D. A.; Medzihradszky, K. F.; Khosla, C.; Stroud, R. M. Nat. Struct. Mol. Biol. 2004, 11, 888-893.
10. Reeves, C. D. Crit. Rev. Biotechnol. 2003, 23, 95-147.
11. Rix, U.; Fischer, C.; Remsing, L. L.; Rohr, J. Nat. Prod. Rep. 2002, 19, 542-580.
12. Mendez, C.; Salas, J. A. Comb. Chem. High Throughput Screening 2003, 6, 513-526.
13. Lee, T. S.; Khosla, C.; Tang, Y. J. Am. Chem. Soc. 2005, 127, 12254-12262.
14. Tang, Y.; Lee, T. S.; Khosla, C. PLoS Biol. 2004, 2, 0227-0238.
15. Jakobi, K.; Hertweck, C. J. Am. Chem. Soc. 2004, 126, 2298-2299.
16. Moore, B. S.; Hertweck, C. Nat. Prod. Rep. 2002, 19, 70-99.
17. Sawada, Y.; Tsuno, T.; Ueki, T.; Yamamoto, H.; Fukagawa, Y.; Oki, T. J. Antibiot. 1993, 46, 507-510.
18. Tsunakawa, M.; Nishio, M.; Ohkuma, H.; Tsuno, T.; Konishi, M.; Naito, T.; Oki, T.; Kawaguchi, H. J. Org. Chem. 1989, 54, 2532-2536.
19. Dairi, T.; Hamano, Y.; Yasuhiro, I.; Furumai, T.; Oki, T. Biosci. Biotechnol. Biochem. 1997, 61, 1445-1453.
20. Dairi, T.; Hamano, Y.; Furumai, T.; Oki, T. Appl. Environ. Microbiol. 1999, 65, 2703-2709.
21. Kitamura, M.; Ohmori, K.; Kawase, T.; Suzuki, K. Angew. Chem. 1999, 111, 1308-1311.
22. Kamachi, H.; Okuyama, S.; Hirano, M.; Masuyoshi, S.; Konishi, M.; Oki, T. J. Antibiot. 1993, 46, 1246-1251.
23. Aburaki, S.; Yamashita, H.; Ohnuma, T.; Kamachi, H.; Moriyama, T. J. Antibiot. 1993, 46, 631-640.
24. Aburaki, S.; Okuyama, S.; Hoshi, H.; Kamachi, H.; Nishio, M.; Hasegawa, T.; Masuyoshi, S.; Imura, S.; Konishi, M.; Oki, T. J. Antibiot. 1993, 46, 1447-1457.
25. Okuyama, S.; Kakushima, M.; Kamachi, H.; Konishi, M.; Oki, T. J. Antibiot. 1993, 46, 500-506.
26. Aoyagi, T.; Aoyama, T.; Kojima, F.; Matsuda, N.; Maruyama, M.; Hamada, M.; Takeuchi, T. J. Antibiot. 1992, 45, 1385-1390.
27. Aliya, S.; Reddanna, P.; Thyagaraju, K. Mol. Cell Biochem. 2003, 253, 319-327.
28. Talalay, P.; De Long, M. J.; Prochaska, H. J. Proc Natl. Acad. Sci. U.S.A. 1988, 85, 8261-8265.
29. McCaughan, F. M.; Brown, A. L.; Harrison, D. J. J. Pathol. 1994, 172, 357-362.
30. Asakura, T.; Ohkawa, K.; Takahashi, N.; Takada, K.; Inoue, T.; Yokoyama, S. Br. J. Cancer 1997, 76, 1333-1337.
31. Kakizaki, I.; Ookawa, K.; Ishikawa, T.; Hayakari, M.; Aoyagi, T.; Tsuchida, S. Jpn. J. Cancer Res. 2000, 91, 1161-1168.
32. Aoyama, T.; Naganawa, H.; Muraoka, Y.; Aoyagi, T.; Takeuchi, T. J. Antibiot. 1992, 45, 1767-1772.
33. Aoyama, T.; Kojima, F.; Abe, F.; Muraoka, Y.; Naganawa, H.; Takeuchi, T.; Aoyagi, T. J. Antibiot. 1993, 46, 914-920.
34. Yamazaki, T.; Tatee, T.; Aoyama, T.; Kojima, F.; Takeuchi, T.; Aoyagi, T. J. Antibiot. 1993, 46, 1309-1311.
35. Höfle, G.; Wolf, H. Liebigs Ann. Chem. 1983, 835-843.
36. Lam, Y. K. T.; Hensens, O.; Helms, G.; Williams, D., Jr.; Nallin, M.; Smith, J.; Gartner, S.; Rodriguez, L. H.; Stevens-Miles, S. Tetrahedron Lett. 1995, 36, 2013-2016.
37. Li, A.; Piel, J. Chem. Biol. 2002, 9, 1017-1026.
38. Masahisa, T.; Shigeru, N.; Hajime, S.; Katsuhisa, O.; Hiroyuki, S. JP8131186; Japan, 1993.
39. Yasushi, S.; Yasunori, F.; Ryuichi, T. JP95 258 153; Japan, 1995.
40. Datsenko, K. A.; Wanner, B. L. Proc Natl. Acad. Sci. U.S.A. 2000, 97, 6640-6645.
41. Murphy, K. C.; Campellone, K. G.; Poteete, A. R. Gene 2000, 246, 321-330.
42. Wendt-Pienkowski, E.; Huang, Y.; Zhang, J.; Li, B.; Jiang, H.; Kwon, H.; Hutchinson, C. R.; Shen, B. J. Am. Chem. Soc. 2005, 127, 16442-16452.
43. Martin, R.; Sterner, O.; Alvarez, M. A.; De Clercq, E.; Bailey, J. E.; Minas, W. J. Antibiot. 2001, 54, 239-249.
44. Summers, R. G.; Wendt-Pienkowski, E.; Motamedi, H.; Hutchinson, C. R. J. Bacteriol. 1992, 174, 1810-1820.
45. Summers, R. G.; Wendt-Pienkowski, E.; Motamedi, H.; Hutchinson, C. R. J. Bacteriol. 1993, 1993, 7571-7580.
46. Shen, B.; Hutchinson, C. R. Science 1993, 262, 1535-1540.
47. Davis, N. K.; Chater, K. F. Mol. Microbiol. 1990, 4, 1679-1691.
48. Davies, C.; Heath, R. J.; White, S. W.; Rock, C. O. Structure 2000, 8, 185-195.
49. Bao, W.; Sheldon, P. J.; Wendt-Pienkowski, E.; Hutchinson, C. R. J. Bacteriol. 1999, 181, 4690-4695.
50. Marti, T.; Hu, Z.; Pohl, N. L.; Shah, A. N.; Khosla, C. J. Biol. Chem. 2000, 275, 33443-33448.
51. Bibb, M. J.; Sherman, D. H.; Omura, S.; Hopwood, D. A. Gene 1994, 142, 31-39.
52. Bililign, T.; Hyun, C.-G.; Williams, J. S.; Czisny, A. M.; Thorson, J. S. Chem. Biol. 2004, 11, 959-969.
53. Cerdeno, A. M.; Bibb, M. J.; Challis, G. L. Chem. Biol. 2001, 8, 817-829.
54. Chater, K. F.; Wilde, L. C. J. Genet. Microbiol. 1980, 116, 323-334.
55. Olano, C.; A. M., R.; Mendez, C.; Salas, J. A. Mol. Microbiol. 1995, 16, 333-343.
56. Aoyama, T.; Naganawa, H.; Muraoka, Y.; Nakamura, H.; Aoyagi, T.; Takeuchi, T.; Iitaka, Y. J. Antibiot. 1992, 45, 1391-1396.
57. Saeed, A. Monatsh. Chem. 2003, 134, 457-463.
58. Bowden, K.; Byrne, J. M. J. Chem. Soc., Perkin Trans. 1996, 2, 1921-1924.
59. Krohn, K.; Bahramsari, R.; Florke, U.; Ludewig, K.; KlicheSpory, C.; Michel, A.; Aust, H. J.; Draeger, S.; Schulz, B.; Antus, S. Phytochemistry 1997, 45, 313-320.
60. Geiger, W. Chem. Ber./Recl. 1974, 107, 2976-2984.
61. Aldrige, D.; Grove, J.; Turner, W. J. Chem. Soc. 1966, 126-128.
62. Tsay, J.-R.; Oh, W. S.; Larson, T. J.; Jackowski, S.; Rock, C. O. J. Biol. Chem. 1992, 267, 6807-6814.
63. Rock, C. O.; Jackowski, S. Biochem. Biophys. Res. Commun. 2002, 292, 1155-1166.
64. Heath, R. J.; Rock, C. O. Nat. Prod. Rep. 2002, 19, 581-596.
65. Smirnova, N.; Reynolds, K. A. J. Bacteriol. 2001, 183, 2335-2342.
66. Li, Y.; Florova, G.; Reynolds, K. A. J. Bacteriol. 2005, 187, 3795-3799.
67. Florova, G.; Kazanina, G.; Reynolds, K. A. Biochemistry 2002, 41, 10462-10471.
68. Tang, Y.; Lee, T. S.; Kobayashi, S.; Khosla, C. Biochemistry 2003, 42, 6588-6595.
69. Meadows, E. S.; Khosla, C. Biochemistry 2001, 40, 14855-14861.
70. Tang, Y.; Lee, N. Y.; Lee, H. Y.; Khosla, C. Tetrahedron 2004, 60, 7659-7671.
71. Han, L.; Lobo, S.; Reynolds, K. A. J. Bacteriol. 1998, 180, 4481-4486.
72. Wallace, K. K.; Zhao, B.; McArthur, H. A.; Reynolds, K. A. FEMS Microbiol. Lett. 1995, 131, 227-234.
73. Rawlings, B. J. Nat. Prod. Rep. 1998, 15, 275-308.
74. Mo, S. J.; Kim, B. S.; Reynolds, K. A. Chem. Biol. 2005, 12, 191-200.
75. Pan, H.; Tsai, S.-C.; Meadows, E. S.; Miercke, L. J. W.; Keatings-Clay, A. T.; O'Connell, J.; Khosla, C.; Stroud, R. M. Structure 2002, 10, 1559-1568.
76. Marti, T.; Hu, Z.; Pohl, N. L.; Shah, A. N.; Khosla, C. J. Biol. Chem. 2000, 275, 33443-33448.
77. Brown, D. W.; Adams, T. H.; Keller, N. P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14873-14877.
78. Schümann, J.; Hertweck, C. J. Biotechnol. 2006, 124, 690-703.
79. Nicholson, T. P.; Winfield, C.; Westcott, J.; Crosby, J.; Simpson, T. J.; Cox, R. J. Chem. Commun. 2003, 686-687.
80. Sontag, B.; Muller, J. G.; Hansske, F. G. J. Antibiot. 2004, 57, 823-828.
81. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning: a Laboratory Manual, 2nd ed.; Cold Spring Harbor: New York, 1989.
82. Scherlach, K.; Partida-Martinez, L. P.; Dahse, H.-M.; Hertweck, C. J. Am. Chem. Soc. 2006, 128, 11529-11536.
83. Ziehl, M.; He, J.; Dahse, H.-M.; Hertweck, C. Angew. Chem. 2005, 117, 4443-4452.