Isotope-effect profiles in the oxidative N-demethylation of N,N-dimethylanilines catalysed by lignin peroxidase and a chemical model

European Journal of Organic Chemistry

Volumn , Issue 12, 2001, Pages 2305-2310

  Baciocchi, Enrico ^a   Gerini, M Francesca ^a   Lanzalunga, Osvaldo ^a   Lapi, Andrea ^a   Lo Piparo, Maria Grazia ^a   Mancinelli, Simona ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Anilines; Enzyme catalysis; Oxidations; Oxidoreductases; Porphyrinoids

Indexed keywords

ANILINE DERIVATIVE; CATION; FERRIC CHLORIDE; ISOTOPE; LIGNIN PEROXIDASE; PORPHYRIN DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; DEMETHYLATION; ELECTRON TRANSPORT; ENZYME MECHANISM; MOLECULAR MODEL; OXIDATION; PKA; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0034977485     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200106)2001:12<2305::AID-EJOC2305>3.0.CO;2-E     Document Type: Article

References (48)

1. [1a] M. Tien, T. K. Kirk, Science 1983, 221, 661-663.
2. [1b] J. K. Glenn, M. A. Morgan, M. B. Mayfield, M. Kuwahara, M. H. Gold, Biochem. Biophys. Res. Commun. 1983, 114, 1077-1083.
3. [1c] H. E. Schoemaker, Recl. Trav. Chim. Pays-Bas 1990, 109, 255-272.
4. [1d] G. Labat, B. Meunier, Bull. Soc. Chim. Fr. 1990, 127, 553-564.
5. [2a] P. J. Kersten, M. Tien, B. Kalyanaraman, T. K. Kirk, J. Biol. Chem. 1985, 260, 2609-2612.
6. [2b] K. E. Hammel, M. D. Mozuch, P. J. Kersten, K. A. Jensen, Biochemistry 1994, 33, 13349-13354 and references therein.
7. [2c] K. Joshi, M. H. Gold, Eur. J. Biochem. 1996, 237, 45-57.
8. [3a] S. D. Haemmerli, M. S. A. Leisola, D. Sanglard, A. Fiechter, J. Biol. Chem. 1986, 261, 6900-6903.
9. [3b] D. K. Joshi, M. H. Gold, Biochemistry 1994, 33, 10969-10976.
10. [3c] D. C. Goodwin, S. D. Aust, T. A. Grover, Biochemistry 1995, 34, 5060-5065.
11. [3d] B. Kalyanaraman, Xenobiotica 1995, 25, 667-675.
12. [3e] A. Paszczynski, S. Goszczynski, R. L. Crawford, D. L. Crawford, Microb. Processes Biorem. 1995, 187.
13. [3f] M. Chivukula, J. T. Spadaro, V. Renganathan, Biochemistry 1995, 34, 7765-7772.
14. E. Baciocchi, M. F. Gerini, O. Lanzalunga, A. Lapi, S. Mancinelli, P. Mencarelli, Chem. Commun. 2000, 393-394.
15. V. Renganathan, M. H. Gold, Biochemistry 1986, 25, 1626-1631.
16. -1).
17. Y. Goto, Y. Watanabe, S. Fukuzumi, J. P. Jones, J. P. Dinnocenzo, J. Am. Chem. Soc. 1998, 120, 10762-10763.
18. J. R. Lindsay-Smith, D. N. Mortimer, J. Chem. Soc., Perkin Trans. 2 1986, 1743-1749.
19. A similar mechanism was proposed for other hemoproteins. O. Okazaki, F. P. Guengerich, J. Biol. Chem. 1993, 268, 1546-1552 and references therein.
20. B. Meunier, in Metalloporphyrins in Catalytic Oxidations (Ed.: R. A. Sheldon), Marcel Dekker, Inc, New York, 1994, Chapter 5.
21. M. Jonsson, D. D. M. Wayner, J. Lusztyk, J. Phys. Chem. 1996, 100, 17539-17543.
22. V. D. Parker, M. Tilset, J. Am. Chem. Soc. 1991, 113, 8778-8781.
23. [16]
24. G. W. Dombrowski, J. P. Dinnocenzo, S. Farid, J. L. Goodman, I. R. Gould, J. Org. Chem. 1999, 64, 427-431.
25. [15a] A. M. de P. Nicholas, D. R. Arnold, Can. J. Chem. 1982, 60, 2165-2179.
26. [15b] F. G. Bordwell, J.-P. Cheng, J. A. Harrelson, Jr., J. Am. Chem. Soc. 1988, 110, 1229-1231.
27. D. D. M. Wayner, V. D. Parker, Acc. Chem. Res. 1993, 26, 287-294.
28. G. Labat, J. L. Séris, B. Meunier, Angew. Chem. Int. Ed. Engl. 1990, 29, 1471-1473.
29. [18a] V. Renganathan, K. Miki, M. H. Gold, Arch. Biochem. Biophys. 1985, 241, 304-314.
30. [18b] M. Tien, T. K. Kirk, C. Bull, J. A. Fee, J. Biol. Chem. 1986, 261, 1687-1693.
31. [18c] A. Andrawis, K. A. Johnson, M. Tien, J. Biol. Chem. 1988, 263, 1195-1198.
32. [18d] H. Wariishi, J. Huang, H. B. Dunford, M. H. Gold, J. Biol. Chem. 1991, 266, 20694-20699.
33. R. A. More O'Ferral, in Proton-Transfer Reactions (Eds.: E. F. Caldin, V. Gold), Chapman and Hall, London, 1975, Chapter 8.
34. S. B. Karki, J. P. Dinnocenzo, J. P. Jones, K. R. Korzekwa, J. Am. Chem. Soc. 1995, 117, 3657-3664.
35. [21a] R. P. Bell, in The Proton in Chemistry, 2nd ed., Cornell University Press, Ithaca, New York, 1973, Chapter 12.
36. [21b] L. Melander, W. H. Saunders, Jr., in Reaction Rates of Isotopic Molecules, Wiley, New York, 1980, Chapter 5.
37. E. Baciocchi, A. Lapi, Tetrahedron Lett. 1999, 5485-5488.
38. [24]
39. J. M. Mayer, in Biomimetic Oxidation Catalysed by Transition Metal Complexes (Ed. B. Meunier), Imperial College Press, London, 2000, Chapter 1.
40. [25a] T. L. Poulos, S. L. Edwards, H. Wariishi, M. H. Gold, J. Biol. Chem. 1993, 268, 4429-4440.
41. [25b] K. Piontek, T. Glumoff, K. Winterhalter, FEBS Lett. 1993, 315, 119-124.
42. [25c] T. Choinowski, W. Blodig, K. H. Winterhalter, K. Piontek, J. Mol. Biol. 1999, 286, 809-827.
43. Preliminary molecular modelling studies seem to indicate that N,N-dimethylaniline may approach the enzyme active site without much hindrance, orienting its aromatic ring parallel to the plane of the heme and its methyl group toward the oxygen of the iron-oxo complex.
44. E. Baciocchi, M. F. Gerini, P. J. Harvey, O. Lanzalunga, S. Mancinelli, Eur. J. Biochem. 2000, 267, 2705-2710 and references therein.
45. M. Tien, T. K. Kirk, Methods Enzymol. 1988, 161, 238-249.
46. M. Tien, T. K. Kirk, C. Bull, J. A. Fee, J. Biol. Chem. 1986, 261, 1687-1693.
47. H. A. Flaschka, A. J. Barnard, Jr., P. E. Sturrock, in Quantitative Analytical Chemistry, Harper & Row, New York, 1969, vol. 2, pp. 149-167.
48. E. B. Fleisher, J. M. Palmer, T. S. Srivastava, A. Chatterjee, J. Am. Chem. Soc. 1971, 93, 3162-3167.