Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula

Journal of Natural Products

Volumn 67, Issue 8, 2004, Pages 1356-1367

  Chang, Zunxue ^a   Sitachitta, Namthip ^b   Rossi, James V ^b   Roberts, Mary Ann ^b   Flatt, Patricia M ^b   Jia, Junyong ^a   Sherman, David H ^a   Gerwick, William H ^b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; COLCHICINE; CURACIN A; CYCLOPROPANE DERIVATIVE; CYSTEINE; HYDROXYMETHYLGLUTARYL COENZYME A SYNTHASE; NATURAL PRODUCT; PEPTIDE SYNTHASE; POLYKETIDE SYNTHASE; S ADENOSYLMETHIONINE; THIAZOLIDINE DERIVATIVE; TOXIN;

ARTICLE; BIOSYNTHESIS; CYANOBACTERIUM; CYTOTOXICITY; DECARBOXYLATION; DRUG BINDING SITE; DRUG DETERMINATION; DRUG STRUCTURE; GENE CASSETTE; GENE CLUSTER; ISOTOPE LABELING; LYNGBYA MAJUSCULA; MICROTUBULE; NETHERLANDS ANTILLES; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEOTIDE SEQUENCE; SEQUENCE ANALYSIS; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANTINEOPLASTIC AGENTS; CYANOBACTERIA; CYCLOPROPANES; MARINE TOXINS; MITOSIS; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SEQUENCE ALIGNMENT; THIAZOLES; TUBULIN MODULATORS;

LYNGBYA MAJUSCULA;

EID: 4344645019     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0499261     Document Type: Article

References (54)

1. Gerwick, W. H.; Tan, L.; Sitachitta, N. The Alkaloids; Academic Press: San Diego, 2001; pp 75-184.
2. Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-48.
3. Bai, R.; Pettit, G. R.; Hamel, E. Biochem. Pharmacol. 1990, 39, 1941-1949.
4. Bai, R.; Friedman, S. J.; Pettit, G. R.; Hamel, E. Biochem. Pharmacol. 1992, 43, 2637-2645.
5. Proteau, P. J.; Gerwick, W. H.; Garcia-Pichel, F.; Castenholz, R. Experientia 1993, 49, 825-829.
6. Gerwick, W. H.; Proteau, P. J.; Nagle, D.; Hamel, E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994, 59, 1243-1245.
7. Blokhin, A. V.; Yoo, H. D.; Geralds, R. S.; Nagle, D. G.; Gerwick, W. H.; Hamel, E. Mol. Pharmacol. 1995, 48, 523-531.
8. Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556-6562.
9. Muir, J. C.; Pattenden, G.; Ye, T. J. Chem. Soc., Perkin Trans. 2002, 2243-2250, and references therein.
10. Verdier-Pinard, P.; Lai, J. Y.; Yoo, H. D.; Yu, J.; Marquez, B.; Nagle, D. G.; Nambu, M.; White, J. D.; Falck, J. R.; Gerwick, W. H.; Day, B. W.; Hamel, E. Mol. Pharmacol. 1998, 53, 62-76.
11. Wipf, P.; Reeves, J. T.; Balachandran, R.; Day, B. W. J. Med. Chem. 2002, 45, 1901-1917.
12. Silakowski, B.; Kunze, B.; Muller, R. Gene 2001, 275, 233-240.
13. Rorrer, G. L.; Modrell, J.; Zhi, C.; Yoo, H.-D.; Nagle, D.; Gerwick, W. H. J. Appl. Phycol. 1995, 7, 187-195.
14. Burja, A. M.; Abou-Mansour, E.; Banaigs, B.; Payri, C.; Burgess, J. G.; Wright, P. C. J. Microbiol. Methods 2002, 48, 207-219.
15. Sitachitta, N.; Rossi, J.; Roberts, M. A.; Gerwick, W. H.; Fletcher, M. D.; Willis, C. L. J. Am. Chem. Soc. 1998, 120, 7131-7132.
16. Williamson, R. T.; Sitachitta, N.; Gerwick, W. H. Tetrahedron 1999, 40, 5175-5178.
17. Sitachitta, N.; Marquez, B. L.; Williamson, R. T.; Rossi, J.; Roberts, M. A.; Gerwick, W. H.; Nguyen, V. A.; Willis, C. L. Tetrahedron 2000, 46, 9103-9114.
18. Chang, Z.; Flatt, P.; Gerwick, W.; Nguyen, V.; Willis, C.; Sherman, D. Gene 2002, 296, 235-247.
19. Flesch, G.; M., R. Eur. J. Biochem. 1988, 175, 405-411.
20. Rohmer, M.; Knani, M.; Simonin, P.; Sutter, B.; Sahm, H. Biochem. J. 1993, 295, 517-524.
21. Vederas, J. C. Nat. Prod. Rep. 1987, 4, 277-337.
22. Weissman, K. J.; Timoney, M.; Bycroft M. G., P.; Hanefeld, U.; Staunton, J.; Leadlay, P. F. Biochemistry 1997, 38, 13849-13855.
23. Lau, J.; Fu, H.; Cane, D. E.; Khosla, C. Biochemistry 1999, 38, 1643-1651.
24. Ershov, Y. V.; Gantt, R. R.; Cunningham, F. X. J.; Gantt, E. J. Bacteriol. 2002, 184, 5045-5051.
25. Abell, C.; Doddrell, D. M.; Garson, M. J.; Laue, E. D.; Staunton, J. J. Chem. Soc., Chem. Commun. 1983, 694-696.
26. Marquez, B.; Verdier-Pinard, P.; Hamel, E.; Gerwick, W. H. Phytochemistry 1998, 49, 2387-2389.
27. Orjala, J.; Gerwick, W. H. J. Nat. Prod. 1996, 59, 427-430.
28. Hooper, G. J.; Orjala, J.; Schatzman, R. C.; Gerwick, W. H. J. Nat. Prod. 1998, 61, 529-533.
29. Orjala, J.; Nagle, D. G.; Hsu, V.; Gerwick, W. H. J. Am. Chem. Soc. 1995, 117, 8281-8282.
30. Orjala, J.; Nagle, D.; Gerwick, W. H. J. Nat. Prod. 1995, 58, 764-768.
31. Piel, J.; Wen, G.; Platzer, M.; Hui, D. ChemBioChem 2004, 5, 93-8.
32. Ligon, J.; Hill, S.; Beck, J.; Zirkle, R.; Molnar, I.; Zawodny, J.; Money, S.; Schupp, T. Gene 2002, 285, 257-267.
33. Wilkinson, C. J.; Frost, E. J.; Staunton, J.; Leadlay, P. F. Chem. Biol. 2001, 8, 1197-1208.
34. Silakowski, B.; Schairer, H. U.; Ehret, H.; Kunze, B.; Weinig, S.; Nordsiek, G.; Brandt, P.; Blocker, H.; Hofle, G.; Beyer, S.; Muller, R. J. Biol. Chem. 1999, 274, 37391-37399.
35. Blokhin, A. V.; Yoo, H. D.; Geralds, R. S.; Nagle, D. G.; Gerwick, W. H.; Hamel, E. Mol. Pharmacol. 1995, 48, 523-531.
36. Edwards, D. J.; Marquez, B.; Nogle, L. M.; McPhail, K.; Goeger, D.; Roberts, M. A.; Gerwick, W. H. Chem. Biol. 2004, in press.
37. Albertini, A. M.; Caramori, T.; Scoffone, F.; Scotti, C.; Galizzi, A. Microbiology 1995, 141, 299-309.
38. El-Sayed, A. K.; Hothersall, J.; Cooper, S. M.; Stephens, E.; Simpson, T. J.; Thomas, C. M. Chem. Biol. 2003, 10, 419-430.
39. Paitan, Y.; Orr, E.; Ron, E. Z.; Rosenberg, E. Microbiology 1999, 145, 3059-3067.
40. Bisang, C.; Long, P. F.; Cortes, J.; Westcott, J.; Crosby, J.; Matharu, A. L.; Cox, R. J.; Simpson, T. J.; Staunton, J.; Leadlay, P. F. Nature 1999, 401, 502-505.
41. Tang, L.; Yoon, Y. J.; Choi, C. Y.; Hutchinson, C. R. Gene 1998, 216, 255-265.
42. Haydock, S. F.; Aparicio, J. F.; Molnar, I.; Schwecke, T.; Khaw, L. E.; Konig, A.; Marsden, A. F.; Galloway, I. S.; Staunton, J.; Leadlay, P. F. FEBS Lett. 1995, 374, 246-248.
43. Silakowski, B.; Nordsiek, G.; Kunze, B.; Blocker, H.; Muller, R. Chem. Biol. 2001, 8, 59-69.
44. Kakavas, S. J.; Katz, L.; Stassi, D. J. Bacteriol. 1997, 179, 7515-7522.
45. Caffrey, P. ChemBioChem 2003, 4, 654-657. Lett. 2002, 4, 1095-1098.
46. Caffrey, P. ChemBioChem 2003, 4, 654-657. Lett. 2002, 4, 1095-1098.
47. Wu, M.; Okino, T.; Nogle, L. M.; Marquez, B. L.; Williamson, R. T.; Sitachitta, N.; Berman, F. W.; Murray, T. F.; McGough, K.; Jacobs, R.; Colsen, K.; Asano, T.; Yokokawa, F.; Shioiri, T.; Gerwick, W. H. J. Am. Chem. Soc. 2000, 122, 12041-12042.
48. Nogle, L. M.; Gerwick, W. H. Org. Lett. 2002, 4, 1095-1098.
49. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning; A Laboratory Manual; Cold Springs Harbor Laboratory Press: New York, 1989.
50. Beyer, S.; Kunze, B.; Silakowski, B.; Muller, R. Biochim. Biophys. Acta 1999, 1445, 185-195.
51. Bierman, M.; Logan, R.; O'Brien, K.; Seno, E. T.; Rao, R. N.; Schoner, B. E. Gene 1992, 116, 43-49.
52. Altschul, S. F.; Madden, T. L.; Schaffer, A. A.; Zhang, J.; Zhang, Z.; Miller, W.; Lipman, D. J. Nucl. Acids Res. 1997, 25, 3389-3402.
53. Challis, G. L.; Ravel, J.; Townsend, C. A. Chem. Biol. 2000, 7, 211-224.
54. Konz, D.; Marahiel, M. A. Chem. Biol. 1999, 6, R39-R48.