Mechanistic studies of the biosynthesis of 2-thiosugar: Evidence for the formation of an enzyme-bound 2-ketohexose intermediate in BexX-catalyzed reaction

Journal of the American Chemical Society

Volumn 132, Issue 44, 2010, Pages 15544-15546

  Sasaki, Eita ^a   Liu, Hung Wen ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHETIC PROTEINS; CATALYZED REACTIONS; COVALENTLY BONDED; D-GLUCOSE; ENZYME-SUBSTRATE COMPLEXES; INSERTION MECHANISM; KETOHEXOSE; LC-MS/MS; MECHANISTIC STUDIES; SITE-SPECIFIC MODIFICATIONS;

BIOCHEMISTRY; ENZYMES; GLUCOSE; REACTION INTERMEDIATES; SUBSTRATES; SULFUR;

BIOSYNTHESIS;

2 THIOSUGAR; ANTIBIOTIC AGENT; BE 7585 A; CARBOHYDRATE DERIVATIVE; GLUCOSE 6 PHOSPHATE; KETOSE; PROTEIN; PROTEIN BEXX; SULFUR; THIAMINE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CARBOHYDRATE SYNTHESIS; CATALYSIS; ENZYME BINDING; ENZYME MODIFICATION; ENZYME SUBSTRATE COMPLEX; MUTAGENESIS;

CATALYSIS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GLUCOSE-6-PHOSPHATE; KETONES; MOLECULAR STRUCTURE; MUTAGENESIS, SITE-DIRECTED; RECOMBINANT PROTEINS; THIOSUGARS;

EID: 78649726941     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja108061c     Document Type: Article

References (36)

1. Weymouth-Wilson, A. C. Nat. Prod. Rep. 1997, 14, 99-110
2. Kren, V. and Martinkova, L. Curr. Med. Chem. 2001, 8, 1303-1328
3. Thorson, J. S., Hosted, J., Jiang, J., Biggins, J. B., and Ahlert, J. Curr. Org. Chem. 2001, 5, 139-167
4. Melancon, C. E., III, Thibodeaux, C. J., and Liu, H.-w. ACS Chem. Biol. 2006, 1, 499-504
5. Mendez, C., Luzhetskyy, A., Bechthold, A., and Salas, J. A. Curr. Top. Med. Chem. 2008, 8, 710-724
6. Williams, G. J., Gantt, R. W., and Thorson, J. S. Curr. Opin. Chem. Biol. 2008, 12, 556-564
7. Solenberg, P. J., Matsushima, P., Stack, D. R., Wilkie, S. C., Thompson, R. C., and Baltz, R. H. Chem. Biol. 1997, 4, 195-202
8. Madduri, K., Kennedy, J., Rivola, G., Inventi-Solari, A., Filippini, S., Zanuso, G., Colombo, A. L., Gewain, K. M., Occi, J. L., MacNeil, D. J., and Hutchinson, C. R. Nat. Biotechnol. 1998, 16, 69-74
9. Yamase, H., Zhao, L., and Liu, H.-w. J. Am. Chem. Soc. 2000, 122, 12397-12398
10. Mendez, C. and Salas, J. A. Trends Biotechnol. 2001, 19, 449-456
11. Griffith, B. R., Langenhan, J. M., and Thorson, J. S. Curr. Opin. Biotechnol. 2005, 16, 622-630
12. Melancon, C. E., III, Yu, W.-l., and Liu, H.-w. J. Am. Chem. Soc. 2005, 127, 12240-12241
13. Melancon, C. E., III and Liu, H.-w. J. Am. Chem. Soc. 2007, 129, 4896-4898
14. Borisova, S. A., Zhang, C., Zhang, H., Takahashi, H., Wong, A., Thorson, J. S., and Liu, H.-w. Angew. Chem., Int. Ed. 2006, 45, 2748-2753
15. He, X., Agnihotri, G., and Liu, H.-w. Chem. Rev. 2000, 100, 4615-4661
16. He, X. M. and Liu, H.-w. Curr. Opin. Chem. Biol. 2002, 6, 590-597
17. He, X. M. and Liu, H.-w. Annu. Rev. Biochem. 2002, 71, 701-754
18. Thibodeaux, C. J., Melancon, C. E., III, and Liu, H.-w. Nature 2007, 446, 1008-1016
19. Thibodeaux, C. J., Melancon, C. E., III, and Liu, H.-w. Angew. Chem., Int. Ed. 2008, 47, 9814-9859
20. Sasaki, E., Ogasawara, Y., and Liu, H.-w. J. Am. Chem. Soc. 2010, 132, 7405-7417
21. Okabe, T., Suda, H., Sato, F., and Okanishi, M. (Banyu Pharmaceutical Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho JP 02-16894 A, 1990.
22. Etoh, H., Iguchi, M., Nagasawa, T., Tani, Y., Yamada, H., and Fukami, H. Agric. Biol. Chem. 1987, 51, 1819-1824
23. Ronning, C. M. and Nierman, W. C. In Myxobacteria: Multicellularity and Differentiation; Whitworth, D. E., Ed.; ASM Press: Washington, DC, 2008; pp 285 - 298.
24. Park, J.-H., Dorrestein, P. C., Zhai, H., Kinsland, C., McLafferty, F. W., and Begley, T. P. Biochemistry 2003, 42, 12430-12438
25. Dorrestein, P. C., Zhai, H., Taylor, S. V., McLafferty, F. W., and Begley, T. P. J. Am. Chem. Soc. 2004, 126, 3091-3096
26. Dorrestein, P. C., Zhai, H., McLafferty, F. W., and Begley, T. P. Chem. Biol. 2004, 11, 1373-1381
27. Mouilleron, S., Badet-Denisot, M. A., and Golinelli-Pimpaneau, B. J. Biol. Chem. 2006, 281, 4404-4412
28. See the Supporting Information for details.
29. Begley, T. P. Nat. Prod. Rep. 2006, 23, 15-25
30. Begley, T. P., Xi, J., Kinsland, C., Taylor, S., and McLafferty, F. Curr. Opin. Chem. Biol. 1999, 3, 623-629
31. Fontecave, M., Ollagnier-de-Choudens, S., and Mulliez, E. Chem. Rev. 2003, 103, 2149-2166
32. Mueller, E. G. Nat. Chem. Biol. 2006, 2, 185-194
33. Kessler, D. FEMS Microbiol. Rev. 2006, 30, 825-840
34. Booker, S. J., Cicchillo, R. M., and Grove, T. L. Curr. Opin. Chem. Biol. 2007, 11, 543-552
35. Jurgenson, C. T., Begley, T. P., and Ealick, S. E. Annu. Rev. Biochem. 2009, 78, 569-603
36. It has been demonstrated that bisulfide can be used as a substitute for the sulfur carrier protein ThiS thiocarboxylate in thiamin biosynthesis. (8) However, this is not the case for BexX, since release of the expected thiosugar product 5 from 11 was not observed in the presence of a high concentration of bisulfide (up to 20 mM).