Structures, reactivities, and antibiotic properties of the marinopyrroles A-F

Journal of Organic Chemistry

Volumn 75, Issue 10, 2010, Pages 3240-3250

  Hughes, Chambers C ^a   Kauffman, Christopher A ^a   Jensen, Paul R ^a   Fenical, William ^a  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

16S RRNA GENE SEQUENCE; ANTI-BACTERIAL ACTIVITY; ANTIBIOTIC PROPERTY; BIPYRROLE; CONFIGURATIONALLY; DEEP OCEAN SEDIMENTS; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; N-BROMOSUCCINIMIDE; NATURAL PRODUCTS; ROOM TEMPERATURE; STREPTOMYCES SPECIES;

BROMINE; CHLORINE; METABOLITES; OCEANOGRAPHY; RNA; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

METABOLISM;

BROMINE; CHLORINE; MARINOPYRROLE A; MARINOPYRROLE B; MARINOPYRROLE C; MARINOPYRROLE D; MARINOPYRROLE E; MARINOPYRROLE F; N BROMOSUCCINIMIDE; NATURAL PRODUCT; PYRROLE DERIVATIVE; RIBOSOME RNA; UNCLASSIFIED DRUG;

ACTINOBACTERIA; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL GENE; BACTERIAL STRAIN; CHEMICAL BOND; CHIRALITY; CONTROLLED STUDY; DRUG STABILITY; DRUG STRUCTURE; GENE SEQUENCE; HALOGENATION; METABOLITE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; NUCLEOTIDE SEQUENCE; ROOM TEMPERATURE; SEQUENCE HOMOLOGY; STREPTOMYCES; STREPTOMYCES SANNURENSIS;

ANTI-BACTERIAL AGENTS; CRYSTALLOGRAPHY, X-RAY; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLES; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM;

EID: 77952515063     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1002054     Document Type: Article

References (54)

1. von Nussbaum, F.; Brands, M.; Hinzen, B.; Weigand, S.; Haebich, D. Angew. Chem., Int. Ed. 2006, 45, 5072-5129
2. Walsh, C. Antibiotics: Actions, Origins, Resistance; ASM Press: Washington, DC, 2003.
3. Schito, G. C. Clin. Microbiol. Infect. 2006, 12, 3-8
4. Palavecino, E. In Methicillin-resistant Staphylococcus Aureus (MRSA) Protocols; Ji, Y., Ed.; Humana Press: Totowa, 2007; pp 1-19.
5. Smith, T. L.; Pearson, M. L.; Wilcox, K. R.; Cruz, C.; Lancaster, M. V.; Robinson-Dunn, B.; Tenover, F. C.; Zervos, M. J.; Band, J. D.; White, E.; Jarvis, W. R. N. Engl. J. Med. 1999, 340, 493-501
6. Maldonado, L. A; Fenical, W.; Jensen, P. R.; Kauffman, C. A.; Mincer, T. J.; Ward, A. C.; Bull, A. T.; Goodfellow, M. Int. J. Syst. Evol. Microbiol. 2005, 55, 1759-1766
7. Fenical, W.; Jensen, P. R. Nat. Chem. Biol. 2006, 2, 666-673
8. Hughes, C. C.; MacMillan, J. B.; Gaudncio, S. P.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2009, 48, 725-727
9. Hughes, C. C.; Prieto-Davo, A.; Jensen, P. R.; Fenical, W. Org. Lett. 2008, 10, 629-631
10. Chang, C.; Adams, R. J. Am. Chem. Soc. 1931, 53, 2353-2357
11. Webb, J. L. A. J. Org. Chem. 1953, 18, 1423-1427
12. Dey, S.; Pal, C.; Nandi, D.; Giri, V. S.; Zaidlewicz, M.; Krzeminski, M.; Smentek, L.; Hess, B. A.; Gawronski, J.; Kwit, M.; Babu, N. J.; Nangia, A.; Jaisankar, P. Org. Lett. 2008, 10, 1373-1376
13. Wu, J.; Vetter, W.; Gribble, G. W.; Schneekloth, J. S., Jr.; Blank, D. H.; Gorls, H. Angew. Chem., Int. Ed. 2002, 41, 1740-1743
14. Mingoia, F. Tetrahedron 2001, 57, 10147-10153
15. Rochais, C.; Lisowski, V.; Dallemagne, P.; Rault, S. Tetrahedron Lett. 2004, 45, 6353-6355
16. Santo, R. D.; Massa, S.; Costi, R.; Simonetti, G.; Retico, A. Farmaco 1994, 49, 229-236
17. Weisburg, W. G.; Barns, S. M.; Pelletier, D. A.; Lane, D. J. J. Bacteriol. 1991, 173, 697-703
18. Fox, G. E.; Wisotzkey, J. D.; Jurtshuk, P., Jr. Int. J. Syst. Bacteriol. 1992, 42, 166-170
19. Stackebrandt, E.; Goebel, B. M. Int. J. Syst. Bacteriol. 1994, 44, 846-849
20. Drancourt, M.; Bollet, C.; Carlioz, A.; Martelin, R.; Gayral, J.-P.; Raoult, D. J. Clin. Microbiol. 2000, 38, 3623-3630
21. Stach, J. E. M.; Maldonado, L. A.; Masson, D. G.; Ward, A. C.; Goodfellow, M.; Bull, A. T. Appl. Environ. Microbiol. 2003, 69, 6189-6200
22. In general, compounds that have few protons have proven to be resistant to confident structure assignment by NMR methods. When H/C ratios reach 0.5 and below, and the number of heteroatoms increases, the use of 2D NMR experiments such as COSY, TOCSY, HMQC, and HMBC are rendered ineffective. Marinopyrrole A has a H/C ratio (nonexchangeable H) of 0.41. This limitation was first described by Professor Phillip Crews, UC Santa Cruz, seventh US-Japan Conference on Marine Natural Products Chemistry (June 2007).
23. The placement of the halogen atom in 3-5, para to the hydroxyl group, agrees with a biosynthetic mechanism involving an electrophilic halogenating species. See: van Pée, K. H. Annu. Rev. Microbiol. 1996, 50, 375-399
24. Hall, D. M.; Harris, M. M. J. Chem. Soc. 1960, 490-494
25. Durham, D. G.; Hughes, C. G.; Rees, A. H. Can. J. Chem. 1972, 50, 3223-3228
26. Petruso, S.; Bonanno, S.; Caronna, S.; Ciofalo, M.; Maggio, B.; Schillaci, D. J. Heterocycl. Chem. 1994, 31, 941-945
27. Takeda, R. J. J. Am. Chem. Soc. 1958, 80, 4749-4750
28. Takeda, R. J. Bull. Agr. Chem. Soc. Jpn. 1959, 23, 126-130
29. Birch, A. J.; Hodge, P.; Rickards, R. W.; Takeda, R.; Watson, T. R. J. Chem. Soc. 1964, 2641-2644
30. Kaneda, M.; Nakamura, S.; Ezaki, N.; Iitaka, Y. J. Antibiot. 1981, 34, 1366-1368
31. Ezaki, N.; Koyama, M.; Shamura, T.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1983, 36, 1263-1267
32. Ezaki, N.; Koyama, M.; Kodama, Y.; Shomura, T.; Tashiro, K.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1983, 36, 1431-1438
33. Vlasov, V. M. Russ. Chem. Rev. 2003, 72, 681-703
34. The imine was resistant to in situ reduction with sodium cyanoborohydride.
35. The atropo purity of 17 degraded slightly, though not enough to account for the 1:1 mixture of diastereomers. The natural product, liberated during prolonged storage of the imine, was isolated in 74% ee.
36. Both H-12 resonances were not clearly resolved from the other aromatic signals.
37. Hughes, C. C.; Yang, Y.-L.; Liu, W.-T.; Dorrestein, P. C.; La Clair, J. J.; Fenical, W. J. Am. Chem. Soc. 2009, 131, 12094-12096
38. Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428-2439
39. Antilla, J, C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578-5587
40. Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem.-Eur. J. 2004, 10, 5607-5622
41. Cai, Q.; Zhu, W.; Zhang, H.; Zhang, Y.; Ma, D. Synthesis 2005, 496-499
42. Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem., Int. Ed. 2007, 46, 934-936
43. Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2007, 46, 8862-8865
44. Mino, T.; Harada, Y.; Shindo, H.; Sakamoto, M.; Fujita, T. Synlett 2008, 614-620
45. For a review of the synthesis of axially chiral biaryl compounds, see: Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384-5427
46. Hasegawa, H.; Shiori, N.; Mogi, K.; Asaoka, T.; Ono, J.; Kuraishi, T.; Katori, T. Jpn. Kokai Tokkyo Koho, Patent no. JP 63183562, 1988.
47. For other examples of pyrrole N -halogenation, see: De Rosa, M. J. Org. Chem. 1982, 47, 1008-1010
48. De Leon, C. Y.; Ganem, B. Tetrahedron 1997, 53, 7731-7752
49. Paparao, C.; Rao, K. V.; Sundaramurthy, V. Synthesis 1981, 234-236
50. Macritchie, J. A.; Silcock, A.; Willis, C. L. Tetrahedron: Asymmetry 1997, 8, 3895-3902
51. Furneaux, R. H.; Tyler, P. C. J. Org. Chem. 1999, 64, 8411-8412
52. Microdilution broth method: Clinical and Laboratory Standards Institute. M7-A8, M100-S19; CLSI: Wayne, PA, 2009.
53. Reference 1d, pp 29-49.
54. MTT method: Mosmann, T J. Immunol. Methods 1983, 65, 55-63