9-mercaptodethiobiotin is generated as a ligand to the [2Fe-2S] + cluster during the reaction catalyzed by biotin synthase from escherichia coli

Journal of the American Chemical Society

Volumn 134, Issue 22, 2012, Pages 9042-9045

  Fugate, Corey J ^a   Stich, Troy A ^b   Kim, Esther G ^b   Myers, William K ^b   Britt, R David ^b   Jarrett, Joseph T ^a  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

9-MERCAPTODETHIOBIOTIN; BIOTIN SYNTHASE; CORRELATION SPECTROSCOPY; DETHIOBIOTIN; ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY; HYDROGEN ATOMS; HYPERFINE COUPLING CONSTANTS; HYPERFINES; HYSCORE; ISOTOPICALLY LABELED; ISOTROPIC COUPLINGS; NUCLEAR SPINS; PARAMAGNETIC CENTERS; REACTION CATALYZED; S-ADENOSYLMETHIONINE; SPIN SYSTEMS; STRUCTURAL MODELS; SULFUR ATOMS;

CATALYSIS; ELECTRON SPIN RESONANCE SPECTROSCOPY; ESCHERICHIA COLI; HYDROGEN; LIGANDS; MODEL STRUCTURES; PARAMAGNETISM; REACTION INTERMEDIATES; SPIN DYNAMICS; SULFUR;

COENZYMES;

9 MERCAPTODETHIOBIOTIN; BIOTIN DERIVATIVE; BIOTIN SYNTHASE; FERROUS SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON SPIN RESONANCE; ENZYME ANALYSIS; ESCHERICHIA COLI; SPECTROSCOPY;

BIOCATALYSIS; BIOTIN; ESCHERICHIA COLI PROTEINS; IRON-SULFUR PROTEINS; LIGANDS; MOLECULAR STRUCTURE; SULFURTRANSFERASES;

EID: 84861839403     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3012963     Document Type: Article

References (29)

1. Booker, S. J.; Cicchillo, R. M.; Grove, T. L. Curr. Opin. Chem. Biol. 2007, 11, 543
2. Marquet, A.; Florentin, D.; Ploux, O.; Tse Sum Bui, B. J. Phys. Org. Chem. 1998, 11, 529
3. Fugate, C. J.; Jarrett, J. T. Biochim. Biophys. Acta 2012, in press.
4. Fontecave, M.; Ollagnier-de-Choudens, S.; Mulliez, E. Chem. Rev. 2003, 103, 2149
5. Marquet, A. Curr. Opin. Chem. Biol. 2001, 5, 541
6. The non-heme iron enzyme, isopenicillin- N -synthase, is a rare example of a metal-oxygen system that can form a C-S bond. Roach, P. L.; Clifton, I. J.; Hensgens, C. M.; Shibata, N.; Schofield, C. J.; Hajdu, J.; Baldwin, J. E. Nature 1997, 387, 827
7. Atta, M.; Arragain, S.; Fontecave, M.; Mulliez, E.; Hunt, J. F.; Luff, J. D.; Forouhar, F. Biochim. Biophy. Acta 2012, in press.
8. Frey, P. A.; Booker, S. J. Adv. Protein Chem. 2001, 58, 1
9. Frey, P. A.; Hegeman, A. D.; Ruzicka, F. J. Crit. Rev. Biochem. Mol. Biol. 2008, 43, 63
10. Cicchillo, R. M.; Booker, S. J. J. Am. Chem. Soc. 2005, 127, 2860
11. Douglas, P.; Kriek, M.; Bryant, P.; Roach, P. L. Angew. Chem., Int. Ed. 2006, 45, 5197
12. Mejean, A.; Bui, B. T.; Florentin, D.; Ploux, O.; Izumi, Y.; Marquet, A. Biochem. Biophys. Res. Commun. 1995, 217, 1231
13. Sanyal, I.; Cohen, G.; Flint, D. H. Biochemistry 1994, 33, 3625
14. Ugulava, N. B.; Sacanell, C. J.; Jarrett, J. T. Biochemistry 2001, 40, 8352
15. Taylor, A. M.; Farrar, C. E.; Jarrett, J. T. Biochemistry 2008, 47, 9309
16. Escalletes, F.; Florentin, D.; Tse Sum Bui, B.; Lesage, D.; Marquet, A. J. Am. Chem. Soc. 1999, 121, 3571
17. Farrar, C. E.; Siu, K. K.; Howell, P. L.; Jarrett, J. T. Biochemistry 2010, 49, 9985
18. Jameson, G. N.; Cosper, M. M.; Hernandez, H. L.; Johnson, M. K.; Huynh, B. H. Biochemistry 2004, 43, 2022
19. Taylor, A. M.; Stoll, S.; Britt, R. D.; Jarrett, J. T. Biochemistry 2011, 50, 7953
20. Berkovitch, F.; Nicolet, Y.; Wan, J. T.; Jarrett, J. T.; Drennan, C. L. Science 2004, 303, 76
21. Höfer, P.; Grupp, A.; Nebenführ, H.; Mehring, M. Chem. Phys. Lett. 1986, 132, 279
22. Stoll, S.; Calle, C.; Mitrikas, G.; Schweiger, A. J. Magn. Reson. 2005, 177, 93
23. Vey, J. L.; Yang, J.; Li, M.; Broderick, W. E.; Broderick, J. B.; Drennan, C. L. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 16137
24. Walsby, C. J.; Hong, W.; Broderick, W. E.; Cheek, J.; Ortillo, D.; Broderick, J. B.; Hoffman, B. M. J. Am. Chem. Soc. 2002, 124, 3143
25. Houseman, A. L. P.; Oh, B. H.; Kennedy, M. C.; Fan, C.; Werst, M. M.; Beinert, H.; Markley, J. L.; Hoffman, B. M. Biochemistry 1992, 31, 2073
26. DeRose, V. J.; Liu, K. E.; Lippard, S. J.; Hoffman, B. M. J. Am. Chem. Soc. 1996, 118, 121
27. Wang, W.; Wang, K.; Li, J.; Nellutla, S.; Smirnova, T. I.; Oldfield, E. J. Am. Chem. Soc. 2011, 133, 8400
28. Silakov, A.; Wenk, B.; Reijerse, E.; Albracht, S. P. J.; Lubitz, W. J. Biol. Inorg. Chem. 2009, 14, 301
29. Farrar, C. E.; Jarrett, J. T. Biochemistry 2009, 48, 2448