Catalytic mechanism of benzylsuccinate synthase, a theoretical study

Journal of Physical Chemistry B

Volumn 106, Issue 31, 2002, Pages 7688-7692

  Himo, Fahmi ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; ENTROPY; PARAMAGNETIC RESONANCE; POTENTIAL ENERGY; PROBABILITY DENSITY FUNCTION; QUENCHING; TOLUENE;

CATALYTIC MECHANISMS;

ENZYMES;

EID: 84961974056     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp014627v     Document Type: Article

References (48)

1. Sawers, G. FEMS Microbiol. Rev. 1999, 22, 543.
2. Buckel, W.; Golding, B. FEMS Microbial. Rev. 1999, 22, 523.
3. Eklund, H.; Fontecave, M. Structure 1999, 7, R257.
4. Stubbe, J.-A.; van der Donk, W. Chem. Rev. 1998, 98, 705.
5. (a) Knappe, J.; Neugebauer, F.A.; Blaschkowski, H.P.; Gänzler, M. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 1332.
6. (b) Wagner, A.F.V.; Frey, M.; Neugebauer, F.A.; Schafer, W.; Knappe, J. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 996.
7. (a) Sun, X.; Harder, J.; Krook, M.; Sjöberg, B.-M.; Reichard, P. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 577.
8. (b) Mulliez, E.; Fontecave, M.; Gaillard, J.; Reichard, P. J. Biol. Chem. 1993, 268, 2296.
9. (c) Sun, X.; Ollaigner, S.; Schmidt, P.P.; Atta, M.; Mulliez, E.; Lepape, L.; Eliasson, R.; Gräslund, A.; Fontecave, M.; Reichard, P.; Sjöberg, B.-M. J. Biol. Chem. 1996, 271, 6827.
10. (d) Young, P.; Andersson, J.; Sahlin, M.; Sjöberg, B.-M. J. Biol. Chem. 1996, 271, 20770.
11. Leuthner, B.; Leutwein, C.; Schulz, H.; Hörth, P.; Haehnel, W.; Schilz, E.; Schägger, H.; Heider, J. Mol. Microbiol. 1998, 28, 615.
12. Krieger, C.J.; Roseboom, W.; Albracht, S.P.J.; Spormann, A.M. J. Biol. Chem. 2001, 276, 12924.
13. (a) Reddy, S.G.; Wong, K.K.; Parast, C.V.; Peisach, J.; Magliozzo, R.S.; Kozarich, J.W. Biochemsitry 1998, 37, 558.
14. (b) Zhang, W.; Wong, K.K.; Magliozzo, R.S.; Kozarich, J.W. Biochemistry 2001, 40, 4123.
15. Gauld, J.W.; Eriksson, L.A. J. Am. Chem. Soc. 2000, 122, 2035.
16. Wong, K.K.; Kozarich, J.W. in Metal Ions in Biological Systems, Vol. 30 Metalloenzymes Involving Amino Acid-Residue and Related Radicals, Sigel, H., Sigel A., Eds.; Marcel Dekker: New York, 1994, p 279.
17. (a) Vieche, H.G.; Meranyi, R.; Stella, L.; Zanousek, Z. Angew. Chem., Int. Ed. Engl. 1979, 18, 917.
18. (b) Vieche, H.G.; Zanousek, Z.; Merenyi, R.; Stella, L. Acc. Chem. Res. 1985, 18, 148.
19. (a) Himo, F. Chem. Phys. Lett. 2000, 328, 270.
20. (b) Himo, F.; Eriksson, L.A. J. Chem. Soc., Perkin Trans. 2 1998, 2, 305.
21. (a) Beller, H.R.; Spormann, A.M. FEMS Microbiol. Lett. 1999, 178, 147.
22. (b) Beller, H.R.; Spormann, A.M. Appl. Environ. Microbiol. 1997, 63, 3729.
23. (c) Beller, H.R.; Spormann, A.M. J. Bacteriol. 1997, 179, 670.
24. (d) Beller, H.R.; Spormann, A.M. J. Bacteriol. 1998, 180, 5454.
25. (e) Coschigano, P.W.; Wehrman, T.S.; Young, L.Y. Appl. Envirnon. Microbiol. 1988, 64, 1650.
26. (a) Becke, A.D. Phys. Rev. 1988, A38, 3098.
27. (b) Becke, A.D. J. Chem. Phys. 1993, 98, 1372.
28. (c) Becke, A.D. J. Chem. Phys. 1993, 98, 5648.
29. Himo, F.; Eriksson, L.A. J. Am. Chem. Soc. 1998, 120, 11449.
30. Cho, K.B.; Himo, F.; Gräslund, A.; Siegbahn, P.E.M. J. Phys. Chem. B 2001, 105, 6445.
31. See for instance (a) Siegbahn, P.E.M.; Crabtree, R.H. J. Am. Chem. Soc. 1997, 119, 3103.
32. (b) Siegbahn, P.E.M. J. Am, Chem. Soc. 1998, 120, 8417.
33. (c) Wirstam, M.; Blomberg, M.R.A.; Siegbahn, P.E.M. J. Am. Chem. Soc. 1999, 121, 10178.
34. (d) Blomberg, M.R.A.; Siegbahn, P.E.M.; Babcock, G.T.; Wikström, M. J. Am. Chem. Soc. 2000, 122, 12848.
35. (e) Wirstam, M.; Siegbahn, P.E.M. J. Am. Chem. Soc. 2000, 122, 8539.
36. (f) Himo, F.; Siegbahn, P.E.M. J. Phys. Chem. B 2000, 104, 7502.
37. (g) Siegbahn, P.E.M. Inorg. Chem. 2000, 39, 2923.
38. (h) Himo, F.; Eriksson, L.A.; Maseras, F.; Siegbahn, P.E.M. J. Am. Chem. Soc. 2000, 122, 8031.
39. (i) Prabhakar, R.; Siegbahn, P.E.M. J. Phys. Chem. B 2001, 105, 4400.
40. (j) Himo, F.; Siegbahn, P.E.M. J. Am. Chem. Soc. 2001, 123, 10280.
41. (k) Blomberg, M.R.A.; Siegbabn, P.E.M. J. Phys. Chem. 2001, 105, 9375.
42. Frisch, M.J.; et al. Gaussian 98, Revision A.9, Gaussian, Inc., Pittsburgh, PA, 1998.
43. (a) Miertus, S.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1981, 114, 117.
44. (b) Miertus, S.; Tomasi, J. J. Chem. Phys. 1982, 65, 239.
45. (c) Cossi, M.; Baroue, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327.
46. (d) Barone, V.; Cossi, M. J. Phys. Chem. 1998, 102, 1995.
47. 16 calculated to be 9.9 kcal/mol. This slight difference originates from the fact that solvent effects were not considered in the PFL study.
48. Ballinger, M.D.; Frey, P.A.; Reed, G.H. Biochemistry 1992, 31, 10782.