The crystal structure and mechanism of an unusual oxidoreductase, GilR, involved in gilvocarcin V biosynthesis

Journal of Biological Chemistry

Volumn 286, Issue 26, 2011, Pages 23533-23543

  Noinaj, Nicholas ^b   Bosserman, Mary A ^a   Schickli, M Alexandra ^a   Piszczek, Grzegorz ^c   Kharel, Madan K ^a,d   Pahari, Pallab ^a   Buchanan, Susan K ^b   Rohr, Jürgen ^a  

^a University of Kentucky   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^c NATIONAL HEART LUNG AND BLOOD INSTITUTE   (United States)

^d Midway College School of Pharmacy   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; ANTI-CANCER AGENTS; ANTI-CANCER THERAPEUTICS; BIOSYNTHETIC PATHWAY; COFACTORS; COVALENT ATTACHMENT; ENZYME ENGINEERING; FUNCTIONAL ASSAYS; HEMIACETALS; HIGH RESOLUTION CRYSTAL STRUCTURE; HISTONE H3; OXIDOREDUCTASES; PHOTO-ACTIVATED; REACTION CATALYSIS; SMALL GROUPS; SUBSTRATE SPECIFICITY;

BIOCHEMISTRY; BIOSYNTHESIS; CATALYSIS; CHROMOPHORES; ENZYMES; KETONES; SUBSTRATES;

CRYSTAL STRUCTURE;

FLAVINE ADENINE NUCLEOTIDE; GILVOCARCIN V; OXIDOREDUCTASE; PROTEIN GILR; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; COVALENT BOND; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME STRUCTURE; ENZYME SUBSTRATE; MUTAGENESIS; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL;

ACTINOBACTERIA; AMINO ACID SUBSTITUTION; BACTERIAL PROTEINS; CATALYSIS; COUMARINS; CRYSTALLOGRAPHY, X-RAY; GLYCOSIDES; MUTAGENESIS, SITE-DIRECTED; MUTATION, MISSENSE; OXIDOREDUCTASES; PROTEIN MULTIMERIZATION; PROTEIN STRUCTURE, QUATERNARY;

EID: 79959540983     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M111.247833     Document Type: Article

References (71)

1. McGee, L. R., and Misra, R. (1990) J. Am. Chem. Soc. 112, 2386-2389
2. Knobler, R. M., Radlwimmer, F. B., and Lane, M. J. (1992) Nucleic Acids Res. 20, 4553-4557
3. Matsumoto, A., and Hanawalt, P. C. (2000) Cancer Res. 60, 3921-3926
4. Alegría, A. E., Zayas, L., and Guevara, N. (1995) Photochem. Photobiol. 62, 409-415
5. Matsumoto, A., Fujiwara, Y., Elespuru, R. K., and Hanawalt, P. C. (1994) Photochem. Photobiol. 60, 225-230
6. Oyola, R., Arce, R., Alegría, A. E., and García, C. (1997) Photochem. Photobiol. 65, 802-810
7. Rohr, J., and Hertweck, C. (2010) in Comprehensive Natural Products II-Chemistry and Biology (Mander, L., and Liu, H. W., eds) pp. 227-303, Elsevier, Oxford
8. Shepherd, M. D., Kharel, M. K., Zhu, L. L., van Lanen, S. G., and Rohr, J. (2010) Org. Biomol. Chem. 8, 3851-3856
9. Elespuru, R. K., and Gonda, S. K. (1984) Science 223, 69-71
10. Yamashita, Y., and Nakano, H. (1988) Nucleic Acids Symp. Ser. 20, 65-67
11. Tse-Dinh, Y. C., and McGee, L. R. (1987) Biochem. Biophys. Res. Commun. 143, 808-812
12. Misra, R., Tritch, H. R., 3rd, and Pandey, R. C. (1985) J. Antibiot. 38, 1280-1283
13. Fischer, C., Lipata, F., and Rohr, J. (2003) J. Am. Chem. Soc. 125, 7818-7819
14. Kharel, M. K., Nybo, S. E., Shepherd, M. D., and Rohr, J. (2010) Chembiochem 11, 523-532
15. Kharel, M. K., Zhu, L., Liu, T., and Rohr, J. (2007) J. Am. Chem. Soc. 129, 3780-3781
16. Liu, T., Fischer, C., Beninga, C., and Rohr, J. (2004) J. Am. Chem. Soc. 126, 12262-12263
17. Kharel, M. K., Pahari, P., Lian, H., and Rohr, J. (2009) Chembiochem 10, 1305-1308
18. Otwinowski, Z., and Minor, W. (1997) Methods Enzymol. 276, 307-326
19. McCoy, A. J. (2007) Acta Crystallogr. D Biol. Crystallogr. 63, 32-41
20. Collaborative Computational Project, N. (1994) Acta Crystallogr. D Biol. Crystallogr. 50, 760-763
21. Winn, M. D. (2003) J. Synchrotron Radiat. 10, 23-25
22. Guex, N., and Peitsch, M. C. (1997) Electrophoresis 18, 2714-2723
23. Emsley, P., and Cowtan, K. (2004) Acta Crystallogr. D Biol. Crystallogr. 60, 2126-2132
24. Adams, P. D., Grosse-Kunstleve, R. W., Hung, L. W., Ioerger, T. R., Mc-Coy, A. J., Moriarty, N. W., Read, R. J., Sacchettini, J. C., Sauter, N. K., and Terwilliger, T. C. (2002) Acta Crystallogr. D Biol. Crystallogr. 58, 1948-1954
25. Lerner, M. G., and Carlson, H. A. (2006) APBS Plugin for PyMOl, University of Michigan, Ann Arbor, MI
26. Wallace, A. C., Laskowski, R. A., and Thornton, J. M. (1995) Protein Eng. 8, 127-134
27. Laue, T. M., Shah, B. D., Ridgeway, T. M., and Pelletier, S. L. (1992) in Analytical Ultracentrifugation in Biochemistry and Polymer Sciences (Harding, S. E., Rowe, A. J., and Horton, J. C., eds) pp. 90-125, Royal Society of Chemistry, Cambridge, UK
28. Lebowitz, J., Lewis, M. S., and Schuck, P. (2002) Protein Sci. 11, 2067-2079
29. Alexeev, I., Sultana, A., Mäntsälä, P., Niemi, J., and Schneider, G. (2007) Proc. Natl. Acad. Sci. U.S.A. 104, 6170-6175
30. Krissinel, E. (2010) J. Comput. Chem. 31, 133-143
31. Krissinel, E., and Henrick, K. (2007) J. Mol. Biol. 372, 774-797
32. Sultana, A., Alexeev, I., Kursula, I., Mäntsälä, P., Niemi, J., and Schneider, G. (2007) Acta Crystallogr. D Biol. Crystallogr. 63, 149-159
33. Huang, C. H., Lai, W. L., Lee, M. H., Chen, C. J., Vasella, A., Tsai, Y. C., and Liaw, S. H. (2005) J. Biol. Chem. 280, 38831-38838
34. Winkler, A., Hartner, F., Kutchan, T. M., Glieder, A., and Macheroux, P. (2006) J. Biol. Chem. 281, 21276-21285
35. Fitzpatrick, P. F. (2004) Bioorg. Chem. 32, 125-139
36. Kutchan, T. M., and Dittrich, H. (1995) J. Biol. Chem. 270, 24475-24481
37. Mattevi, A., Fraaije, M. W., Mozzarelli, A., Olivi, L., Coda, A., and van Berkel, W. J. (1997) Structure 5, 907-920
38. Gille, C., and Frömmel, C. (2001) Bioinformatics 17, 377-378
39. Clamp, M., Cuff, J., Searle, S. M., and Barton, G. J. (2004) Bioinformatics 20, 426-427
40. Waterhouse, A. M., Procter, J. B., Martin, D. M., Clamp, M., and Barton, G. J. (2009) Bioinformatics 25, 1189-1191
41. Holm, L., and Rosenström, P. (2010) Nucleic Acids Res. 38, W545-W549
42. Wheeler, G. L., Jones, M. A., and Smirnoff, N. (1998) Nature 393, 365-369
43. Glock, G. E., and McLean, P. (1952) Nature 170, 119-120
44. Bashiri, G., Squire, C. J., Moreland, N. J., and Baker, E. N. (2008) J. Biol. Chem. 283, 17531-17541
45. Borchardt, J. K. (1999) Modern Drug Discovery 2, 22-29
46. Baig, I., Perez, M., Braña, A. F., Gomathinayagam, R., Damodaran, C., Salas, J. A., Méndez, C., and Rohr, J. (2008) J. Nat. Prod. 71, 199-207
47. Cropp, T. A., Kim, B. S., Beck, B. J., Yoon, Y. J., Sherman, D. H., and Reynolds, K. A. (2002) Biotechnol. Genet. Eng. Rev. 19, 159-172
48. Floss, H. G. (2006) J. Biotechnol. 124, 242-257
49. Hutchinson, C. R. (1998) Curr. Opin. Microbiol. 1, 319-329
50. Hutchinson, C. R. (2000) in Drug Discovery From Nature, pp. 233-254, Springer, Heidelberg, Germany
51. Khosla, C., and Zawada, R. J. X. (1996) Trends Biotechnol. 14, 335-341
52. Leadlay, P. F. (1997) Curr. Opin. Chem. Biol. 1, 162-168
53. Luzhetskyy, A., and Bechthold, A. (2005) Mol. Microbiol. 58, 3-5
54. Menzella, H. G., and Reeves, C. D. (2007) Curr. Opin. Microbiol. 10, 238-245
55. Olano, C., Méndez, C., and Salas, J. A. (2010) Nat. Prod. Rep. 27, 571-616
56. Remsing, L. L., González, A. M., Nur-e-Alam, M., Fernández-Lozano, M. J., Braña, A. F., Rix, U., Oliveira, M. A., Méndez, C., Salas, J. A., and Rohr, J. (2003) J. Am. Chem. Soc. 125, 5745-5753
57. Sánchez, C., Zhu, L., Braña, A. F., Salas, A. P., Rohr, J., Méndez, C., and Salas, J. A. (2005) Proc. Natl. Acad. Sci. U.S.A. 102, 461-466
58. Staunton, J., and Wilkinson, B. (2001) Curr. Opin. Chem. Biol. 5, 159-164
59. Van Lanen, S. G., and Shen, B. (2006) Drug Discovery Today: Technologies 3, 285-292
60. Walsh, C. T. (2002) Chembiochem 3, 125-134
61. Weissman, K. J., and Leadlay, P. F. (2005) Nat. Rev. Microbiol. 3, 925-936
62. Zhang, W., and Tang, Y. (2008) J. Med. Chem. 51, 2629-2633
63. Zhou, H., Xie, X., and Tang, Y. (2008) Curr. Opin. Biotechnol. 19, 590-596
64. Carter, G. T., Fantini, A. A., James, J. C., Borders, D. B., and White, R. J. (1984) Tetrahedron Lett. 25, 255-258
65. Carter, G. T., Fantini, A. A., James, J. C., Borders, D. B., and White, R. J. (1985) J. Antibiot. 38, 242-248
66. Takahashi, K., and Tomita, F. (1983) J. Antibiot. 36, 1531-1535
67. Heuts, D. P., Scrutton, N. S., McIntire, W. S., and Fraaije, M. W. (2009) FEBS J. 276, 3405-3427
68. Winkler, A., Kutchan, T. M., and Macheroux, P. (2007) J. Biol. Chem. 282, 24437-24443
69. Leferink, N. G., Heuts, D. P., Fraaije, M. W., and van Berkel, W. J. (2008) Arch. Biochem. Biophys. 474, 292-301
70. Huang, C. H., Winkler, A., Chen, C. L., Lai, W. L., Tsai, Y. C., Macheroux, P., and Liaw, S. H. (2008) J. Biol. Chem. 283, 30990-30996
71. Beam, M. P., Bosserman, M. A., Noinaj, N., Wehenkel, M., and Rohr, J. (2009) Biochemistry 48, 4476-4487