Cloning and biochemical characterization of the hectochlorin biosynthetic gene cluster from the marine cyanobacterium Lyngbya majuscula

Journal of Natural Products

Volumn 70, Issue 12, 2007, Pages 1977-1986

  Ramaswamy, Aishwarya V ^a   Sorrels, Carla M ^a,b   Gerwick, William H ^a,b,c  

^a OREGON STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDROXYISOVALERIC ACID; 5,5 DICHLOROHEXANOIC ACID; ANTIFUNGAL AGENT; CEREULIDE; CRYPTOPHYCIN DERIVATIVE; DOLABELLIN; HECTOCHLORIN; HEXANOIC ACID DERIVATIVE; JAMAICAMIDE A; JAMAICAMIDE B; JAMAICAMIDE C; KETOREDUCTASE; LYNGBYABELLIN A; LYNGBYABELLIN B; NATURAL PRODUCT; OXIDOREDUCTASE; PEPTIDE SYNTHASE; UNCLASSIFIED DRUG; VALINOMYCIN;

ANIMAL CELL; ARTICLE; BIOSYNTHESIS; CHEMICAL ANALYSIS; CONTROLLED STUDY; CYANOBACTERIUM; CYTOKINESIS; DNA SEQUENCE; DRUG ISOLATION; DRUG POTENCY; FUNGICIDAL ACTIVITY; GENE CLUSTER; GENE EXPRESSION; LYNGBYA MAJUSCULA; MOLECULAR CLOCK; NONHUMAN; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; RAT;

AMINO ACID SEQUENCE; CYANOBACTERIA; DNA, BACTERIAL; GENES, BACTERIAL; LACTONES; MARINE BIOLOGY; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; SEQUENCE ANALYSIS, PROTEIN; THIAZOLES;

CHLOROPHYTA; CYANOBACTERIA; LYNGBYA MAJUSCULA;

EID: 38349022535     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0704250     Document Type: Article

References (60)

1. Newman, D. J.; Cragg, G. M.; Snader, K. M. J. Nat. Prod. 2003, 66, 1022-1037.
2. Burja, A. M.; Banaigs, B.; Abou-Mansour, E.; Burgess, J. G.; Wright, P. C. Tetrahedron 2001, 57, 9347-9377.
3. Gerwick, W. H.; Tan, L.; Sitachitta, N. The Alkaloids; Academic Press: San Diego, 2001; Vol. 57, pp 75-184.
4. Van Wagoner, R. M.; Drummond, A. K.; Wright, J. L. C. Adv. Appl. Microbiol. 2007, 61, 89-213.
5. Finking, R.; Marahiel, M. Annu. Rev. Microbiol. 2004, 58, 453-488.
6. Weissman, K. J. Philos. Transact. A Math. Phys. Eng. Sci. 2004, 362, 2671-2690.
7. Marquez, B. L.; Watts, K. S.; Yokochi, A.; Roberts, M. A.; Verdier-Pinard, P.; Jimenez, J. I.; Hamel, E.; Scheuer, P. J.; Gerwick, W. H. J. Nat. Prod. 2002, 65, 866-871.
8. Sone, H.; Kondo, T.; Kiruyu, M.; Ishiwata, H.; Ojika, M.; Yamada, K. J. Org. Chem. 1995, 60, 4774-4781.
9. Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J.; Mooberry, S. L. J. Nat. Prod. 2000, 63, 611-615.
10. Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2000, 63, 1437-1439.
11. Milligan, K. E.; Marquez, B. L.; Williamson, R. T.; Gerwick, W. H. J. Nat. Prod. 2000, 63, 1440-1443.
12. Cetusic, J. R. P.; Green, F. R.; Graupner, P. R.; Oliver, M. P. Org. Lett. 2002, 4, 1307-1310.
13. Chang, Z.; SitachittaN.; Rossi, J. V.; Roberts, M. A.; FlattP. M.; Jia, J.; Sherman, D. H.; Gerwick, W. H. J. Nat. Prod. 2004, 67, 1356-1367.
14. Williamson, R. T.; Sitachitta, N.; Gerwick, W. H. Tetrahedron 1999, 40, 5175-5178.
15. Neilan, B. A.; Dittmann, E.; Rouhiainen, L.; Bass, R. A.; Schaub, V.; Sivonen, K.; Borner, T. J. Bacteriol. 1999, 181, 4089-4097.
16. Edwards, D. J.; Marquez, B. L.; Nogle, L. M.; McPhail, K.; Goeger, D. E.; Roberts, M. A.; Gerwick, W. H. Chem. Biol. 2004, 11, 817-833.
17. Beyer, S.; Kunze, B.; Silakowski, B.; Muller, R. Biochim. Biophys. Acta 1999, 1445, 185-195.
18. Chang, Z.; Flatt, P.; Gerwick, W. H.; Nguyen, V. A.; Willis, C. L.; Sherman, D. H. Gene 2002, 296, 235-247.
19. Edwards, D. J.; Gerwick, W. H. J. Am. Chem. Soc. 2004, 126, 11432-11433.
20. Ullrich, M.; Bender, C. L. J. Bacteriol. 1994, 176, 7574-7586.
21. Guenzi, E.; Galli, G.; Grgurina, I.; Gross, D. C.; Grandi, G. J. Biol. Chem. 1998, 273, 32857-32863.
22. Zhang, J. H.; Quigley, N. B.; Gross, D. C. J. Bacteriol. 1995, 177, 4009-4020.
23. Mukherji, M.; Chien, W.; Kershaw, N. J.; Clifton, I. J.; Schofield, C. J.; Wierzbicki, A. S.; Lloyd, M. D. Hum. Mol. Genet. 2001, 10, 1971-1982.
24. Censini, S.; Lange, C.; Xiang, Z.; Crabtree, J. E.; Ghiara, P.; Borodovsky, M.; Rappuoli, R.; Covacci, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14648-14653.
25. Murai, N.; Kamata, H.; Nagashima, Y.; Yagisawa, H.; Hirata, H. Gene 1995, 163, 103-107.
26. Bancroft, I.; Wolk, C. P. J. Bacteriol. 1989, 171, 5949-5954.
27. Donadio, S.; Staver, M. J. Gene 1993, 126, 147-151.
28. Moffitt, M. C.; Neilan, B. A. Appl. Environ. Microbiol. 2004, 70, 6353-6362.
29. Tillett, D.; Dittmann, E.; Erhard, M.; von Dohren, H.; Borner, T.; Neilan, B. A. Chem. Biol. 2000, 7, 753-764.
30. Ehling-Schulz, M.; Vukov, N.; Schulz, A.; Shaheen, R.; Andersson, M.; Martlbauer, E.; Scherer, S. Appl. Environ. Microbiol. 2005, 71, 105-113.
31. Du, L.; Chen, M.; Sanchez, C.; Shen, B FEMS Microbiol. Lett. 2000, 189, 171-175.
32. Paitan, Y.; Orr, E.; Ron, E. Z.; Rosenberg, E. Gene 1999, 228, 147-153.
33. Stachelhaus, T.; Mootz, H. D.; Marahiel, M. A. Chem. Biol. 1999, 6, 493-505.
34. Kershaw, N. J.; Mukherji, M.; MacKinnon, C. H.; Claridge, T. D.; Odell, B.; Wierzbicki, A. S.; Lloyd, M. D.; Schofield, C. J. Bioorg. Med. Chem. 2001, 11, 2545-2548.
35. Flatt, P. M.; O'Connell, S. J.; McPhail, K. L.; Zeller, G.; Willis, C. L.; Sherman, D. H.; Gerwick, W. H. J. Nat. Prod. 2006, 69, 938-944.
36. Galonić, D. P.; Vaillancourt, F. H.; Walsh, C. T. J. Am. Chem. Soc. 2006, 128, 3900-3901.
37. Vaillancourt, F. H.; Yin, J.; Walsh, C. T. Proc. Natl. Acad. Sci. 2005, 102, 10111-10116.
38. Vaillancourt, F. H.; Yeh, E.; Vosburg, D. A.; O'Connor, S. E.; Walsh, C. T. Nature 2005, 436, 1191-1194.
39. Mahillon, J.; Chandler, M. Microbiol. Mol. Biol. Rev. 1998, 62, 725-774.
40. Mahillon, J.; Leonard, C.; Chandler, M. Res. Microbiol. 1999, 150, 675-687.
41. Becker, J. E.; Moore, R. E.; Moore, B. S. Gene 2004, 325, 35-42.
42. Christiansen, G.; Fastner, J.; Erhard, M.; Borner, T.; Dittmann, E. J. Bacteriol. 2003, 185, 564-72.
43. 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.
44. Challis, G. L.; Ravel, J.; Townsend, C. A. Chem. Biol. 2000, 7, 211-224.
45. Cheng, Y. ChemBioChem 2006, 7, 471-477.
46. Magarvey, N. A.; Beck, Z. Q.; Golakoti, T.; Ding, Y.; Huber, U.; Hemschidt, T. K.; Abelson, D.; Moore, R. E.; Sherman, D. H. ACS Chem. Biol. 2006, 1, 766-779.
47. Kuse, M.; Franz, T.; Koga, K.; Suwan, S.; Isobe, M.; Agata, N.; Ohta, M. Bioorg. Med. Chem. Lett. 2000, 10, 735-739.
48. Magarvey, N. A.; Ehling-Schulz, M.; Walsh, C. T. J. Am. Chem. Soc. 2006, 128, 10698-10699.
49. Reid, R.; Piagentini, M.; Rodriguez, E.; Ashley, G.; Viswanathan, N.; Carney, J.; Santi, D. V.; Hutchinson, C. R.; McDaniel, R. Biochemistry 2003, 42, 72-79.
50. Varon, M.; Fuchs, N.; Monosov, M.; Tolchinsky, S.; Rosenberg, E. Antimicrob. Agents Chemother. 1992, 36, 2316-2321.
51. Andersen, J. F.; Hutchinson, C. R. J. Bacteriol. 1992, 174, 725-735.
52. Molnar, I.; Schupp, T.; Ono, M.; Zirkle, R.; Milnamow, M.; Nowak-Thompson, B.; Engel, N.; Toupet, C.; Stratmann, A.; Cyr, D. D.; Gorlach, J.; Mayo, J. M.; Hu, A.; Goff, S.; Schmid, J.; Ligon, J. M. Chem. Biol. 2000, 7, 97-109.
53. Chen, H.; Walsh, C. T. Chem. Biol. 2001, 8, 301-312.
54. Chen, H.; Hubbard, B. K.; O'Connor, S. E.; Walsh, C. T. Chem. Biol. 2002, 9, 103-112.
55. Chen, H.; Thomas, M. G.; O'Connor, S. E.; Hubbard, B. K.; Burkart, M. D.; Walsh, C. T. Biochemistry 2001, 40, 11651-11659.
56. Schwarzer, D.; Finking, R.; Marahiel, M. A. Nat. Prod. Rep. 2003, 20, 275-287.
57. Schneider, T. L.; Shen, B.; Walsh, C. T. Biochemistry 2003, 42, 9722-9730.
58. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning: A Laboratory Manual, 2nd ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1989.
59. Thompson, J. D.; Higgins, D. G.; Gibson, T. J. Nucleic Acids Res. 1994, 22, 4673-4680.
60. Hanson, R. L.; Singh, J.; Kissick, T. P.; Patel, R. N.; Szarka, L. J.; Mueller, R. H. Bioorg. Chem. 1990, 18, 116-130.