A diverted total synthesis of mycolactone analogues: An insight into buruli ulcer toxins

Chemistry - A European Journal

Volumn 17, Issue 51, 2011, Pages 14413-14419

  Chany, Anne Caroline ^a   Casarotto, Virginie ^a   Schmitt, Marjorie ^a   Tarnus, Céline ^a   Guenin Macé, Laure ^b   Demangel, Caroline ^b   Mirguet, Olivier ^c   Eustache, Jacques ^a   Blanchard, Nicolas ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

^b INSTITUT PASTEUR   (France)

^c GLAXOSMITHKLINE   (France)

Author keywords

Buruli ulcer; metathesis; mycolactones; structure activity relationships; total synthesis

Indexed keywords

BURULI ULCER; METATHESIS; MYCOLACTONES; STRUCTURE ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS;

CELL CULTURE; DISEASES;

METABOLITES;

BACTERIAL TOXIN; MACROLIDE; MYCOLACTONE; MYCOLACTONE A; MYCOLACTONE B;

ANIMAL; ARTICLE; BURULI ULCER; CHEMICAL STRUCTURE; CHEMICALLY INDUCED DISORDER; CHEMISTRY; DRUG EFFECT; FIBROBLAST; MICROBIOLOGY; MOUSE; MYCOBACTERIOSIS; MYCOBACTERIUM ULCERANS; PATHOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; BACTERIAL TOXINS; BURULI ULCER; FIBROBLASTS; MACROLIDES; MICE; MOLECULAR STRUCTURE; MYCOBACTERIUM INFECTIONS; MYCOBACTERIUM ULCERANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 83755195577     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102542     Document Type: Article

References (63)

1. K. M. George, D. Chatterjee, G. Gunawardana, D. Welty, J. Hayman, R. Lee, P. L. C. Small, Science 1999, 283, 854
2. G. Gunawardana, D. Chatterjee, K. M. George, P. Brennan, D. Whittern, P. L. C. Small, J. Am. Chem. Soc. 1999, 121, 6092.
3. J. Rohr, Angew. Chem. 2000, 112, 2967
4. Angew. Chem. Int. Ed. 2000, 39, 2847.
5. M. T. Silva, F. Portaels, J. Pedrosa, Lancet Infect. Dis. 2009, 9, 699
6. C. Demangel, T. P. Stinear, S. T. Cole, Nat. Rev. Microbiol. 2009, 10, 50
7. D. S. Walsh, F. Portaels, W. M. Meyers, Clin. Microbiol. Newsl. 2009, 31, 119
8. H. Hong, C. Demangel, S. J. Pidot, P. F. Leadlay, T. Stinear, Nat. Prod. Rep. 2008, 25, 447
9. M. Wansbrough-Jones, R. Phillips, The Lancet 2006, 367, 1849
10. V. Sizaire, F. Nackers, E. Comte, F. Portaels, Lancet Infect. Dis. 2006, 6, 288
11. P. D. R. Johnson, T. Stinear, P. L. C. Small, G. Pluschke, R. W. Merritt, F. Portaels, K. Huygen, J. A. Hayman, K. Asiedu, PLoS. Med 2005, 2, e 108
12. T. van der Werf, T. Stinear, Y. Stienstra, W. T. A. van der Graaf, P. L. Small, Lancet 2003, 362, 1062.
13. S. J. Pidot, K. Asiedu, M. Käser, J. A. M. Fyfe, T. P. Stinear, PLoS. Negl. Trop. Dis. 2010, 4, e 663.
14. W. A. Nienhuis, Y. Stienstra, W. A. Thompson, P. C. Awuah, K. M. Abass, W. Tuah, N. Y. Awua-Boateng, E. O. Ampadu, V. Siegmund, J. P. Schouten, O. Adjei, G. Bretzel, T. S. van der Werf, The Lancet 2010, 375, 664
15. S. Etuaful, B. Carbonnelle, J. Grosset, S. Lucas, C. Horsfield, R. Phillips, M. Evans, D. Ofori-Adjei, E. Klustse, J. Owusu-Boateng, G. K. Amedofu, P. Awuah, E. Ampadu, G. Amofah, K. Asiedu, M. Wansbrough-Jones, Antimicrob. Agents Chemother. 2005, 49, 3182.
16. T. S. van der Werf, W. T. A. van der Graaf, J. W. Tappero, K. Asiedu, Lancet 1999, 354, 1013.
17. A. B. Benowitz, S. Fidanze, P. L. C. Small, Y. Kishi, J. Am. Chem. Soc. 2001, 123, 5128
18. S. Fidanze, F. Song, M. Szlosek-Pinaud, P. L. C. Small, Y. Kishi, J. Am. Chem. Soc. 2001, 123, 10117
19. Y. Kishi, Proc. Natl. Acad. Sci. USA 2011, 108, 6703.
20. Mycolactones A/B
21. K. L. Jackson, W. Li, C.-L. Chen, Y. Kishi, Tetrahedron 2010, 66, 2263
22. F. Song, S. Fidanze, A. B. Benowitz, Y. Kishi, Tetrahedron 2007, 63, 5379
23. F. Song, S. Fidanze, A. B. Benowitz, Y. Kishi, Org. Lett. 2002, 4, 647; Mycolactone C
24. T. C. Judd, A. Bischoff, Y. Kishi, S. Adusumilli, P. L. C. Small, Org. Lett. 2004, 6, 4901; Mycolactone E
25. S. Aubry, R. E. Lee, E. A. Mahrous, P. L. C. Small, D. Beachboard, Y. Kishi, Org. Lett. 2008, 10, 5385; Mycolactone F
26. H.-J. Kim, Y. Kishi, J. Am. Chem. Soc. 2008, 130, 1842; Mycolactone dia-F
27. H.-J. Kim, K. L. Jackson, Y. Kishi, H. R. Williamson, L. Mosi, P. L. C. Small, Chem. Commun. 2009, 7402; Minor metabolite
28. T. Spangenberg, S. Aubry, Y. Kishi, Tetrahedron Lett. 2010, 51, 1782.
29. T. Spangenberg, Y. Kishi, Chem. Commun. 2010, 46, 1410.
30. G. Wang, N. Yin, E.-i. Negishi, Chem. Eur. J. 2011, 17, 4118
31. N. Yin, G. Wang, M. Qian, E.-i. Negishi, Angew. Chem. 2006, 118, 2982
32. Angew. Chem. Int. Ed. 2006, 45, 2916. M. K.
33. P. Gersbach, A. Jantsch, F. Feyen, N. Scherr, J.-P. Dangy, G. Pluschke, K.-H. Altmann, Chem. Eur. J. 2011, 17, 13017
34. F. Feyen, A. Jantsch, K.-H. Altmann, Synlett 2007, 3, 415.
35. M. K. Gurjar, J. Cherian, Heterocycles 2001, 55, 1095.
36. K.-S. Ko, M. D. Alexander, S. D. Fontaine, J. E. Biggs-Houck, J. J. La Clair, M. D. Burkart, Org. Biomol. Chem. 2010, 8, 5159
37. M. D. Alexander, S. D. Fontaine, J. J. La Clair, A. G. DiPasquale, A. L. Rheingold, M. D. Burkart, Chem. Commun. 2006, 4602.
38. R. P. van Summeren, B. L. Feringa, A. J. Minnaard, Org. Biomol. Chem. 2005, 3, 2524.
39. A. Fürstner, Isr. J. Chem. 2011, 51, 329
40. P. A. Wender, B. A. Loy, A. J. Schrier, Isr. J. Chem. 2011, 51, 453
41. A. M. Szpilman, E. M. Carreira, Angew. Chem. 2010, 122, 9786
42. Angew. Chem. Int. Ed. 2010, 49, 9592
43. R. M. Wilson, S. J. Danishefsky, Angew. Chem. 2010, 122, 6168
44. Angew. Chem. Int. Ed. 2010, 49, 6032
45. R. M. Wilson, S. J. Danishefsky, J. Org. Chem. 2006, 71, 8329.
46. D. S. Snyder, P. L. C. Small, Microb. Pathogenesis 2003, 34, 91.
47. H. Hong, T. Stinear, J. Porter, C. Demangel, P. F. Leadlay, ChemBioChem 2007, 8, 2043.
48. U. S. Racherla, H. C. Brown, J. Org. Chem. 1991, 56, 401
49. H. C. Brown, K. S. Bhat, R. S. Randad, J. Org. Chem. 1987, 52, 320
50. H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2091.
51. C. Aïssa, R. Riveiros, J. Ragot, A. Fürstner, J. Am. Chem. Soc. 2003, 125, 15512.
52. G. W. Kabalka, T. M. Shoup, N. M. Goudgaon, J. Org. Chem. 1989, 54, 5930.
53. A. Guérinot, S. Reymond, J. Cossy, Angew. Chem. 2007, 119, 6641
54. Angew. Chem. Int. Ed. 2007, 46, 6521; see also
55. G. Cahiez, C. Duplais, A. Moyeux, Org. Lett. 2007, 9, 3253; For a recent review, see
56. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500.
57. N. Hamon, N. Blanchard, unpublished results.
58. G. A. O'Doherty, T. J. Hunter, Org. Lett. 2001, 3, 1049.
59. D. M. Hodgson, L. T. Boulton, G. N. Maw, Tetrahedron 1995, 51, 3713.
60. G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054.
61. Y. Kaburagi, Y. Kishi, Org. Lett. 2007, 9, 723.
62. To evaluate the relevance of plasma protein binding on in vitro potency, cytopathic assays were run in complete medium (Eagle's MEM supplemented with 10% horse serum). A negligible shift in potency was observed (data not shown). For a review, see:, D. A. Smith, L. Di, E. H. Kerns, Nat. Rev. 2010, 9, 929.
63. A. Mve-Obiang, R. E. Lee, F. Portaels, P. L. C. Small, Infect. Immun. 2003, 71, 774.