Photochemistry of mycolactone A/B, the causative toxin of buruli ulcer

Journal of the American Chemical Society

Volumn 134, Issue 46, 2012, Pages 19234-19239

  Xing, Yalan ^a   Hande, Sudhir M ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HOMOGENEOUS MATERIALS; PHOTOCHEMICAL TRANSFORMATIONS; PHOTOPRODUCTS; SINGLET STATE; STRUCTURE DETERMINATION; VISIBLE LIGHT;

UNSATURATED FATTY ACIDS;

CYCLOADDITION;

LACTONE DERIVATIVE; MYCOLACTONE A; MYCOLACTONE B; PENTAENOIC ACID; TETRAENOIC ACID; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

ARTICLE; BURULI ULCER; CYCLOADDITION; CYTOTOXICITY; LIGHT; PHOTOCHEMISTRY; STRUCTURE ANALYSIS;

BURULI ULCER; HUMANS; MACROLIDES; MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES; STEREOISOMERISM;

EID: 84869441013     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja309215m     Document Type: Article

References (39)

1. Portaels, F., Johnson, P., Meyers, W., Eds. Buruli Ulcer: Mycobacterium ulcerans infection; World Health Organization: Geneva, Switzerland, 2001.
2. Hong, H.; Demangel, C.; Pidot, S. J.; Leadlay, P. F.; Stinear, T. Nat. Prod. Rep. 2008, 25, 447
3. Kishi, Y. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 6703
4. For example, see a review: Converse, P. J.; Nuermberger, E. L.; Almeida, D. V.; Grosset, J. H. Future Microbiol. 2011, 6, 1185
5. George, K. M.; Chatterjee, D.; Gunawardana, G.; Welty, D.; Hayman, J.; Lee, R.; Small, P. L. C. Science 1999, 283, 854
6. George, K. M.; Pascopella, L.; Welty, D. M.; Small, P. L. C. Infect. Immun. 2000, 68, 877
7. Gunawardana, G.; Chatterjee, D.; George, K. M.; Brennan, P.; Whittern, D.; Small, P. L. C. J. Am. Chem. Soc. 1999, 121, 6092
8. Benewoitz, A. B.; Fidanze, S.; Small, P. L. C.; Kishi, Y. J. Am. Chem. Soc. 2001, 123, 5128
9. Fidanze, S.; Song, F.; Szlosek-Pinaud, M.; Small, P. L. C.; Kishi, Y. J. Am. Chem. Soc. 2001, 123, 10117
10. Song, F.; Fidanze, S.; Benowitz, A. B.; Kishi, Y. Org. Lett. 2002, 4, 647
11. Tetrahedron 2007, 63, 5739.
12. Jackson, K. L.; Li, W.; Chen, C.-L.; Kishi, Y. Tetrahedron 2010, 66, 2263
13. Negishi group: Yin, N.; Wang, G.; Qian, M.; Negishi, E. Angew. Chem., Int. Ed. 2006, 45, 2916
14. Wang, G.; Yin, N.; Negishi, E. Chem. Eur. J. 2011, 17, 4118
15. Altmann group: Feyen, F.; Jantsch, A.; Altmann, K.-H. Synlett 2007, 415
16. Gersbach, P.; Jantsch, A.; Feyen, F.; Scherr, N.; Dangy, J.-P.; Pluschke, G.; Altmann, K.-H. Chem. Eur. J. 2011, 17, 13017
17. Chany, A.-C.; Casarotto, V.; Schmitt, M.; Tarnus, C.; Guenin-Mace, L.; Demangel, C.; Mirguet, O.; Eustache, J.; Blanchard, N. Chem. Eur. J. 2011, 17, 14413
18. Burkart group: Alexander, M. D.; Fontaine, S. D.; La Clair, J. J.; DiPasquale, A. G.; Rheingold, A. L.; Burkart, M. D. Chem. Commun. 2006, 4602
19. Feringa group: van Summeren, R. P.; Feringa, B. L.; Minnaard, A. J. Org Biomol. Chem. 2005, 3, 2524
20. Huber, T. W.; Reddick, R. A.; Kubica, G. P. Appl. Microbiol. 1970, 19, 383
21. Even-Paz, Z.; Haas, H.; Sacks, T.; Rosenmann, E. Br. J. Dermatol. 1976, 94, 435
22. Cope, R. B.; Hartman, J. A.; Morrow, C. K.; Haschek, W. M.; Small, P. L. C. Photodermatol. Photoimmunol. Photomed. 2002, 18, 271
23. For example, see: Woodward, R. B.; Hoffmann, R. W. In The Conservation of Orbital Symmetry; VCH: Weinheim, 1970; pp 79-81.
24. Dauben, W. G.; Bell, I.; Hutton, T. W.; Laws, G. F.; Rheiner, A., Jr.; Urscheler, H. J. Am. Chem. Soc. 1958, 80, 4116
25. Saunderson, C. P. Acta Crystallogr. 1965, 19, 187
26. Ireland, C.; Scheuer, P. J. Science 1979, 205, 922
27. Ireland, C.; Faulkner, J. Tetrahedron 1981, 37, 233
28. Kobayashi, Y.; Tan, C.-H.; Kishi, Y. Helv. Chim. Acta 2000, 83, 2562
29. Higashibayashi, S.; Czechtizky, W.; Kobayashi, Y.; Kishi, Y. J. Am. Chem. Soc. 2003, 125, 14379
30. Miller, A. K.; Trauner, D. Angew. Chem., Int. Ed. 2003, 42, 549
31. Miller, A. K.; Trauner, D. Synlett 2006, 2295 and references cited therein.
32. For an example related to this case in a broad sense, see: Budt, K.-H.; Vatele, J.-M.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 6080
33. Turro, N. J. Page 257 In Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991.
34. Griesbeck, A. G.; Mattay, J. Synthetic Organic Photochemistry; Marcel Dekker: New York, 2005; p 1.
35. Bruückner, S.; Baldwin, J. E.; Moses, J.; Adlington, R. M.; Cowley, A. R. Tetrahedron Lett. 2003, 44, 7471
36. Moses, J. E.; Baldwin, J. E.; Marquez, R.; Adlington, R. M.; Claridge, T. D. W.; Odell, B. Org. Lett. 2003, 5, 661
37. For example, see: Hong, H.; Coutanceau, E.; Leclerc, M.; Caleechurn, L.; Leadlay, P. F.; Demangel, C. PLoS Neglected Trop. Dis. 2008, 2, e325
38. 50 = 2020 nM (10-A1) vs 13 nM (1)), Hek-293 (2510 vs 3.3), Sk-Mel-5 (3600 vs 12), Sk-Mel-28 (470 vs 4.5), and A549 (3820 vs 4.7). Hande, S. M.; Xing, Y.; Burgett, A.; Shair, M. D.; Kishi, Y. Details of this study shall be reported elsewhere.
39. Marion, E.; Prado, S.; Cano, C.; Babonneau, J.; Ghamrawi, S.; Marsollier, L. PLoS ONE 2012, 7, e33600