Structural basis for the enantioselectivity of an epoxide ring opening reaction catalyzed by halo alcohol dehalogenase HheC

Journal of the American Chemical Society

Volumn 127, Issue 38, 2005, Pages 13338-13343

  De Jong, René M ^a   Tiesinga, Jan J W ^a   Villa, Alessandra ^a   Tang, Lixia ^a   Janssen, Dick B ^a   Dijkstra, Bauke W ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; HYDROGEN BONDS; NITROGEN COMPOUNDS; STEREOCHEMISTRY; STYRENE;

ENANTIOSELECTIVITY; EPOXIDES; REGIOSELECTIVE RING OPENING; RING OPENING REACTION;

AROMATIC COMPOUNDS;

ALCOHOL DEHALOGENASE; AZIDE; CYANIDE; EPOXIDE; HALIDE; HALOALCOHOL; HALOALCOHOL DEHALOGENASE HHEC; NITROSTYRENE OXIDE; STYRENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; CRYSTALLOGRAPHY; DEHALOGENATION; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; HYDROGEN BOND; RING OPENING; X RAY ANALYSIS;

ALCOHOLS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; EPOXY COMPOUNDS; HYDROGEN BONDING; HYDROLASES; MODELS, MOLECULAR; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; STEREOISOMERISM;

EID: 25444448270     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0531733     Document Type: Article

References (38)

1. Kazlauskas, R. J. Curr. Opin. Chem. Biol. 2000, 4, 81-88.
2. Bornscheuer, U. T. Curr. Opin. Biotechnol. 2002, 13, 543-547.
3. Reetz, M. T. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5716-5722.
4. Faber, K.; Kroutil, W. Curr. Opin. Chem. Biol. 2005, 9, 181-187.
5. van Hylckama Vlieg, J. E. T.; Tang, L.; Lutje Spelberg, J. H.; Smilda, T.; Poelarends, G. J.; Bosma, T.; van Merode, A. E. J.; Fraaije, M. W.; Janssen, D. B. J. Bacteriol. 2001, 183, 5058-5066.
6. de Vries, E. J.; Janssen, D. B. Curr. Opin. Biotechnol. 2003, 14, 414-420.
7. de Jong, R. M.; Tiesinga, J. J. W.; Rozeboom, H. J.; Kalk, K. H.; Tang, L.; Janssen, D. B.; Dijkstra, B. W. EMBO J. 2003, 22, 4933-4944.
8. Lutje Spelberg, J. H.; van Hylckama Vlieg, J. E. T.; Tang, L.; Janssen, D. B.; Kellogg, R. M. Org. Lett. 2001, 3, 41-43.
9. Lutje Spelberg, J. H.; Tang, L.; van Gelder, M.; Kellogg, R. M.; Janssen, D. B. Tetrahedron: Asymmetry 2002, 13, 1083-1089.
10. Lutje Spelberg, J. H.; Tang, L.; Kellogg, R. M.; Janssen, D. B. Tetrahedron: Asymmetry 2004, 15, 1095-1102.
11. Hasnaoui, G.; Lutje Spelberg, J. H.; de Vries, E.; Tang, L.; Hauer, B.; Janssen, D. B. Tetrahedron: Asymmetry 2004, 15, 1095-1102.
12. Tang, L.; Lutje Spelberg, J. H.; Fraaije, M. W.; Janssen, D. B. Biochemistry 2003, 42, 5378-5386.
13. Tang, L.; van Merode, A. E. J.; Lutje Spelberg, J. H.; Fraaije, M. W.; Janssen, D. B. Biochemistry 2003, 42, 14057-14065.
14. Lutje Spelberg, J. H. University of Groningen, Groningen, The Netherlands. Personal communication, 2004.
15. de Jong, R. M.; Rozeboom, H. J.; Kalk, K. H.; Tang, L.; Janssen, D. B.; Dijkstra, B. W. Acta Crystallogr., Sect. D 2002, 58, 176-178.
16. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
17. Kleywegt, G. J.; Jones, T. A. Acta Crystallogr., Sect. D 1998, 54, 1119-1131.
18. McRee, D. E. J. Struct. Biol. 1999, 125, 156-165.
19. Kraulis, P. J. J. Appl. Crystallogr. 1991, 24, 946-950.
20. Merritt, E. A.; Bacon, D. J. Methods Enzymol. 1997, 277, 505-524.
21. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; Hermans, J. In Intermolecular Forces; Pullman, B., Ed.; Reidel: Dordrecht, The Netherlands, 1981; pp 131-137.
22. van Gunsteren, W. F.; Billeter, S. R.; Eising, A. A.; Hünenberger, P. H.; Krüger, P.; Mark, A. E.; Scott, W. R. P.; Tironi, I. G. Biomolecular simulation: GROMOS96 Manual and User Guide; Hochschulverlag AG an der ETH Zürich: Zürich, Switzerland, 1996.
23. Schuler, L. D.; van Gunsteren, W. F. Mol. Simul. 2000, 25, 301-319.
24. Schiott, B.; Bruice, T. C. J. Am. Chem. Soc. 2002, 124, 14558-14570.
25. Berendsen, H. J. C.; van der Spoel, D.; van Drunen, R. Comput. Phys. Commun. 1995, 91, 43-56.
26. van der Spoel, D.; van Buuren, A. R.; Apol, E.; Meulenhoff, P. J.; Tieleman, D. P.; Sijbers, A. L. T. M.; Hess, B.; Feenstra, K. A.; Lindahl, E.; van Drunen, R.; Berendsen, H. J. C. Gromacs User Manual, version 3.0; University of Groningen: Groningen, The Netherlands, 2001 (http://www.gromacs.org).
27. Lindahl, E.; Hess, B.; van der Spoel, D. J. Mol. Model. 2001, 7, 306-317.
28. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684-3690.
29. Miyamoto, S.; Kollman, P. A. J. Comput. Chem. 1992, 13, 952-962.
30. Hess, B.; Bekker, H.; Berendsen, H. J. C.; Fraaije, J. G. E. M. J. Comput. Chem. 1997, 18, 1463-1472.
31. Mark, A. E. In Encyclopedia of Computational Chemistry; von Rague Schleyer, P., Ed.; Wiley: New York, 1998; pp 1070-1083.
32. Beutler, T. C.; Mark, A. E.; van Schaik, R. C.; Geber, P. R.; van Gunsteren, W. F. Chem. Phys. Lett. 1994, 222, 529-539.
33. Villa, A.; Mark, A. E. J. Comput. Chem. 2002, 23, 548-553.
34. Bishop, M.; Frinks, S. J. Chem. Phys. 1987, 87, 3675-3676.
35. Allen, M. P.; Tildesley, D. J. Computer Simulations of Liquids; Oxford Science Publications; Oxford, 1987.
36. Fersht, A. R.; Shi, J. P.; Knill-Jones, J.; Lowe, D. M.; Wilkinson, A. J.; Blow, D. M.; Brick, P.; Carter, P.; Waye, M. M.; Winter, G. Nature 1985, 314, 235-238.
37. Shue, S.-Y.; Yang, D.-Y.; Selzle, H. L.; Schlag, E. W. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 12683-12687.
38. Brünger, A. T.; Adams, P. D.; Rice, L. M. Structure 1997, 5, 325-336.