Mechanism-based inactivation by aromatization of the transaminase BioA involved in biotin biosynthesis in mycobaterium tuberculosis

Journal of the American Chemical Society

Volumn 133, Issue 45, 2011, Pages 18194-18201

  Shi, Ce ^a   Geders, Todd W ^b   Park, Sae Woong ^c   Wilson, Daniel J ^a   Boshoff, Helena I ^d   Abayomi, Orishadipe ^d,e   Barry, Clifton E ^d   Schnappinger, Dirk ^c   Finzel, Barry C ^b   Aldrich, Courtney C ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c WEILL CORNELL MEDICAL COLLEGE   (United States)

^d NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES   (United States)

^e Chemistry Advanced Laboratory   (Nigeria)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUBERCULAR AGENTS; BIOCHEMICAL CHARACTERIZATION; BIOTIN BIOSYNTHESIS; COFACTORS; CONCENTRATION-DEPENDENT; HETEROCYCLES; M. TUBERCULOSIS; MECHANISM OF ACTION;

BIOCHEMISTRY; COENZYMES; X RAY CRYSTALLOGRAPHY;

BIOSYNTHESIS;

BIOTIN; PYRIDOXAL 5 PHOSPHATE; SUICIDE SUBSTRATE;

AROMATIZATION; ARTICLE; BACTERIUM MUTANT; BIOSYNTHESIS; CHEMICAL ANALYSIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; COVALENT BOND; ENZYME INACTIVATION; ENZYME SYNTHESIS; GENE SILENCING; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTEIN EXPRESSION; X RAY CRYSTALLOGRAPHY;

ANTITUBERCULAR AGENTS; BACTERIAL PROTEINS; BIOCATALYSIS; BIOTIN; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; PYRIDONES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSAMINASES;

EID: 80755126602     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja204036t     Document Type: Article

References (61)

1. World Health Organization. Global tuberculosis control 2010. http://www.who.int/tb/-publications/global-report/2010/en/index.html (last accessed 04/13/11).
2. Koul, A.; Arnoult, E.; Lounis, N.; Guillemont, J.; Andries, K. Nature 2011, 469, 483
3. Barry, C. E., 3rd; Blanchard, J. S. Curr. Opin. Chem. Biol. 2010, 14, 456
4. Aldrich, C. C.; Boshoff, H. I.; Remmel, R. P. Antitubercular Agents. In Burgers Medicinal Chemistry, 7 th ed.; Rotella, D.; Abraham, D. J., Eds.; Wiley: New York, 2010; p 713.
5. Marquet, A.; Bui, B. T. S.; Florentin, D. Vit. Horm. 2001, 61, 51
6. Dey, S.; Lane, J. M.; Lee, R. E.; Rubin, E. J.; Sacchettini, J. C. Biochemistry 2010, 49, 6746
7. Sassetti, C. M.; Rubin, E. J. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 12989
8. Park, S. W.; Klotzsche, M.; Wilson, D. J.; Boshoff, H. I.; Eoh, H.; Manjunatha, U.; Blumenthal, A.; Rhee, K.; Barry, C. E., 3rd; Aldrich, C. C.; Ehrt, S.; Schnappinger, D. PloS Pathog. 2011, 7, e1002264
9. Bhor, V. M.; Dev, S.; Vasanthakumar, G. R.; Kumar, P.; Sinha, S.; Surolia, A. J. Biol. Chem. 2006, 281, 25076
10. Mann, S. and Ploux, O. Biochim. Biophys. Acta 2011, 1814 (11) 1459
11. Mann, S.; Ploux, O. FEBS J. 2006, 273, 4778
12. Mann, S.; Colliandre, L.; Labesse, G.; Ploux, O. Biochimie 2009, 91, 826
13. Escalettes, F.; Florentin, D.; Bui, B. T. S.; Lesage, D.; Marquet, A. J. Am. Chem. Soc. 1999, 121, 3571
14. Farrar, C. E.; Siu, K. K. W.; Howell, P. L.; Jarrett, J. T. Biochemistry 2010, 49, 9985
15. Lin, S.; Hanson, R. E.; Cronan, J. E. Nat. Chem. Biol. 2010, 6, 682
16. Okami, Y.; Kitahara, T.; Hamada, M.; Naganawa, H.; Kondo, S. J. Antibiot. 1974, 27, 656
17. Kitahara, T.; Hotta, K.; Yoshida, M.; Okami, Y. J. Antibiot. 1975, 28, 215
18. Hotta, K.; Kitahara, T.; Okami, Y. J. Antibiot. 1975, 28, 222
19. Poetsch, M.; Zahner, H.; Werner, R. G.; Kern, A.; Jung, G. J. Antibiot. 1985, 38, 312
20. Mann, S.; Carillon, S.; Breyne, O.; Marquet, A. Chem.-Eur. J. 2002, 8, 439
21. Sandmark, J.; Mann, S.; Marquet, A.; Schneider, G. J. Biol. Chem. 2002, 277, 43352
22. Mann, S.; Florentin, D.; Lesage, D.; Drujon, T.; Ploux, O.; Marquet, A. Helv. Chim. Acta 2003, 86, 3836
23. Orisadipe, A.; Boshoff, H. I.; Barry, C. E., 3rd Unpublished results.
24. Olson, G. T.; Fu, M.; Lau, S.; Rinehart, K. L.; Silverman, R. B. J. Am. Chem. Soc. 1998, 120, 2256
25. Fu, M.; Nikolic, D.; Van Breemen, R. B.; Silverman, R. B. J. Am. Chem. Soc. 1999, 121, 7751
26. Fu, M.; Silverman, R. B. Bioorg. Med. Chem. 1999, 7, 1581
27. Fu, M.; Silverman, R. B. Bioorg. Med. Chem. Lett. 2004, 14, 203
28. Wang, Z.; Yuan, H.; Nikolic, D.; Van Breemen, R. B.; Silverman, R. B. Biochemistry 2006, 45, 14513
29. Liu, D.; Pozharski, E.; Lepore, B. W.; Fu, M.; Silverman, R. B.; Petsko, G. A.; Ringe, D. Biochemistry 2007, 46, 10517
30. Lepore, B. W.; Liu, D.; Peng, Y.; Fu, M.; Yasuda, C.; Manning, J. M.; Silverman, R. B.; Ringe, D. Biochemistry 2010, 49, 3138
31. Liu, D.; Pozharski, E.; Fu, M.; Silverman, R. B.; Ringe, D. Biochemistry 2010, 49, 10507
32. Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412
33. Perez-Fuertes, Y.; Kelly, A. M.; Johnson, A. L.; Arimori, S.; Bull, S. D.; James, T. D. Org. Lett. 2006, 8, 609
34. Daniel, R. N.; Melancon, B. J.; Wang, E. A.; Crews, B. C.; Marnett, L. J.; Sulikowski, G. A.; Lindsley, C. W. J. Org. Chem. 2009, 74, 8852
35. Berkowitz, D. B.; Maiti, G. Org. Lett. 2004, 6, 2661
36. Hallian, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 24, 3537
37. Li, H.; Jiang, X.; Ye, Y.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1, 91
38. Jiang, W.; Wanner, J.; Lee, R. J.; Bounaud, P.-Y.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 5288
39. Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791
40. Wilson, D. J.; Shi, C.; Duckworth, B. P.; Muretta, J. M.; Manjunatha, U.; Sham, Y. Y.; Thomas, D. D.; Aldrich, C. C. Anal. Biochem. 2011, 416, 27
41. Copeland, R. A. Irreversible Enzyme Inactivators. Evaluation of Enzyme Inhibitors in Drug Discovery; Wiley & Sons: Hoboken, N.J., 2005; p 214.
42. Garcia-Fandino, R.; Aldegunde, M. J.; Codesido, E. M.; Castedo, L.; Granja, J. R. J. Org. Chem. 2005, 70, 8281
43. Pflugrath, J. W. Acta Crystallogr., D: Biol. Crystallogr. 1999, 55, 1718
44. McCoy, A. J.; Grosse-Kunstleve, R. W.; Adams, P. D.; Winn, M. D.; Storoni, L. C.; Read, R. J. J. Appl. Crystallogr. 2007, 40, 658
45. Collaborative Computational Project, Number 4. Acta Crystallogr., D: Biol. Crystallogr. 1994, 50, 760.
46. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallogr., D: Biol. Crystallogr. 1997, 53, 240
47. Emsley, P.; Cowtan, K. Acta Crystallogr., D: Biol. Crystallogr. 2004, 60, 2126
48. Schuttelkopf, A. W.; van Aalten, D. M. Acta Crystallogr., D: Biol. Crystallogr. 2004, 60, 1355
49. Adams, P. D. Acta Crystallogr., D: Biol. Crystallogr. 2010, 66, 213
50. Davis, I. W.; Murray, L. W.; Richardson, J. S.; Richardson, D. C. Nucleic Acids Res. 2004, 32, W615
51. DeLano, W. L. The PyMOL molecular graphics system; DeLano Scientific: Palo Alto, CA, 2002.
52. Cook, M. J.; Katritzky, A. R.; Linda, P.; Tack, R. D. Chem. Commun. 1971, 510
53. Singh, J.; Petter, R. C.; Baillie, T. A.; Whitty, A. Nat. Rev. Drug Discovery 2011, 10, 307
54. Lu, H.; Tonge, P. J. Curr. Opin. Chem. Biol. 2010, 14, 467
55. Cerqueira, N. M. F. S. A.; Fernandes, P. A.; Ramos, M. J. J. Chem. Theory Comput. 2011, 7, 1356-1368
56. Oliveira, E. F. O., Cerqueira, N. M. F. S. A., Fernandes, P. A., and Ramos, M. J. J. Am. Chem. Soc. 2011, 133 (39) 15496
57. Nanavati, S. M.; Silverman, R. B. J. Med. Chem. 1989, 32, 2413
58. Lowther, J.; Yard, B. A.; Johnson, K. A.; Carter, L. G.; Bhat, V. T.; Raman, M. C.; Clarke, D. J.; Ramakers, B.; McMahon, S. A.; Naismith, J. H.; Campopiano, D. J. Mol. Biosyst. 2010, 6, 1682
59. Bird, C. W. Tetrahedron 1985, 41, 1409
60. Bird, C. W. Tetrahedron 1986, 42, 89
61. Nishino, T.; Murao, S.; Wada, H. J. Biochem. 1984, 95, 1283