Enzyme catalytic promiscuity: The nonheme Fe2+ center of β-diketone-cleaving dioxygenase Dke1 promotes hydrolysis of activated esters

ChemBioChem

Volumn 11, Issue 4, 2010, Pages 502-505

  Leitgeb, Stefan ^a   Nidetzky, Bernd ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Enzyme catalysis; Esterase activity; Metalloenzymes; Nonheme iron; Zinc

Indexed keywords

1,3 DIKETONE; DIOXYGENASE; ENZYME; ESTER; IRON; PROTEIN DKE1; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; CATALYSIS; ENZYME ACTIVE SITE; ENZYME ACTIVITY; HYDROLYSIS; KINETICS; PRIORITY JOURNAL;

ACINETOBACTER; COENZYMES; DIOXYGENASES; ESTERS; HYDROLYSIS; IRON; METALLOPROTEINS; MODELS, MOLECULAR;

EID: 77149120453     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900688     Document Type: Article

References (44)

1. a) M. D. Toscano, K. J. Woycechowsky, D. Hilvert, Angew. Chem. 2007, 119, 3274-3300;
2. Angew. Chem. Int. Ed. 2007, 46, 3212-3236;
3. b) I. Nobeli, A. D. Favia, J. M. Thornton, Nat. Biotechnol. 2009, 27, 157-167;
4. c) N. Tokuriki, D. S. Tawfik, Science 2009, 324, 203-207;
5. d) C. Li, M. Hassler, T. D. Bugg, ChemBioChem 2008, 9, 71-76;
6. e) L. L. Lairson, A. G. Watts, W. W. Warkachuk, S. G. Withers, Nat. Chem. Biol. 2006, 2, 724-728;
7. f) O. Khersonsky, C. Roodveldt, D. S. Tawfik, Curr. Opin. Chem. Biol. 2006, 10, 498-508;
8. g) P. J. O'Brien, D. Herschlag, Chem. Biol. 1999, 6, 91-105.
9. a) K. Hult, P. Berglund, Trends Biotechnol. 2007, 25, 231-238;
10. b) R. J. Kazlauskas, Curr. Opin. Chem. Biol. 2005, 9, 195-201;
11. c) U. T. Bornscheuer, R. J. Kazlauskas, Angew. Chem. Int. Ed. 2004, 43, 6032-6040.
12. a) H. Jochens, K. Stiba, C. Saville, R. Fujii, J. G. Yu, T. Gerassenkov, R. J. Kazlauskas, U. T. Bornscheuer, Angew. Chem. 2009, 121, 3584-3587;
13. Angew. Chem. Int. Ed. 2009, 48, 3532 -3535;
14. b) R. Kourist, S. Bartsch, L. Fransson, K. Hult, U. T. Bornscheuer, ChemBioChem 2008, 9, 67-69;
15. c) I. Sanchez-Moreno, L. Iturrate, R. Martin-Hoyos, M. L. Jimeno, M. Mena, A. Bastida, E. Garcia-Junceda, ChemBioChem 2009, 10, 225-229;
16. d) K. Okrasa, R. J. Kazlauskas, Chem. Eur. J. 2006, 12, 1587-1596;
17. e) A. Fernandez-Gacio, A. Codina, J. Fastrez, O. Riant, P. Soumillon, ChemBioChem 2006, 7, 1013-1016;
18. f) Q. Jing, K. Okrasa, R. J. Kazlauskas, Chem. Eur. J. 2009, 15, 1370-1376.
19. a) G. D. Straganz, A. Glieder, L. Brecker, D. W. Ribbons, W. Steiner, Biochem. J. 2003, 369, 573-581;
20. b) G. D. Straganz, H. Hofer, W. Steiner, B. Nidetzky, J. Am. Chem. Soc. 2004, 126, 12202-12203;
21. c) G. D. Straganz, B. Nidetzky, ChemBioChem 2006, 7, 1536-1548;
22. d) S. Leitgeb, B. Nidetzky, Biochem. Soc. Trans. 2008, 36, 1180-1186.
23. S. Leitgeb, G. D. Straganz, B. Nidetzky, Biochem. J. 2009, 418, 403-411.
24. a) S. Chai, W.-L. Wang, Q.-Z. Ye, J. Biol. Chem. 2008, 283, 26879-26885;
25. b) M. Leopoldini, N. Russo, M. Toscano, J. Am. Chem. Soc. 2007, 129, 7776-7784.
26. On definition and use of enzyme catalytic proficiency: a) X. Zhang, K. N. Houk, Acc. Chem. Res. 2005, 38, 379-385;
27. b) B. G. Miller, R. Wolfenden, Annu. Rev. Biochem. 2002, 71, 847-885.
28. X. Zhang, J. DeChancie, H. Gunaydin, A. B. Chowdry, F. R. Clemente, A. J. T. Smith, T. M. Handel, K. N. Houk, J. Org. Chem. 2008, 73, 889-899.
29. V. M. Krishnamurthy, G. K. Kaufman, A. R. Urbach, I. Gitlin, K. L. Gudiksen, D. B. Weibel, G. M. Whitesides, Chem. Rev. 2008, 108, 946-1051.
30. a) C. Letondor, T. R. Ward, ChemBioChem 2006, 7, 1845-1852;
31. b) M. Creus, T. R. Ward, Org. Biomol. Chem. 2007, 5, 1835-1844.
32. a) Y. Pocker, M. W. Beug, Biochemistry 1972, 11, 698-707;
33. b) A. Thorslund, S. Lindskog, Eur. J. Biochem. 1967, 3, 117-123;
34. c) B. Elleby, B. Sjöblom, S. Lindskog, Eur. J. Biochem. 1999, 262, 516-521;
35. d) S. M. Gould, D. S. Tawfik, Biochemistry 2005, 44, 5444-5452;
36. e) G. Höst, L.-G. Mårtensson, B.-H. Jonsson, Biochim. Biophys. Acta 2006, 1764, 1601-1606;
37. f) G. Höst, B.-H. Jonsson, Biochim. Biophys. Acta 2008, 1784, 811-815.
38. a) T. D. H. Bugg, Tetrahedron 2003, 59, 7075-7101;
39. b) T. D. H. Bugg, G. Lin, Chem. Commun. 2001, 941-952;
40. c) J. Sanvoisin, G. J. Langley, T. D. H. Bugg, J. Am. Chem. Soc. 1995, 117, 7836-7837.
41. G. F. Z. da Silva, L.-J. Ming, J. Am. Chem. Soc. 2005, 127, 16380-16381.
42. F. van de Velde, L. Kçnemann, F. van Rantwijk, R. A. Sheldon, Biotechnol. Bioeng. 2000, 67, 87-96.
43. J. M. Dunwell, A. Purvis, S. Khuri, Phytochemistry 2004, 65, 7-17.
44. 2+, however, not an esterase; X. E. Wells, E. M. Lees, Arch. Biochem. Biophys. 1991, 287, 151-159.