Oxidation of non-phenolic substrates with the laccase/N-hydroxyacetanilide system: Structure of the key intermediate from the mediator and mechanistic insight

New Journal of Chemistry

Volumn 28, Issue 3, 2004, Pages 366-372

  Cantarella, Gaetano ^a   Galli, Carlo ^a   Gentili, Patrizia ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE DERIVATIVE; BENZYL ALCOHOL; HYDROGEN; ISOTOPE; LACCASE; N HYDROXYACETANILIDE; OXYGEN; PHENOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; ELECTRON TRANSPORT; ENERGY; ENZYME SUBSTRATE; HYDROGEN BOND; HYPOTHESIS; KINETICS; MOLECULAR INTERACTION; OXIDATION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 1642289306     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b311907f     Document Type: Article

References (58)

1. A. Messerschmidt, Multi-Copper Oxidases, World Scientific, Singapore, 1997.
2. R. ten Have and P. J. M. Teunissen, Chem. Rev., 2001, 101, 3397-3413.
3. M. Tien and T. K. Kirk, Science, 1983, 221, 661-663.
4. M. Kuwahara, J. K. Glenn, A. Morgan and M. H. Gold, FEBS Lett., 1984, 169, 247-250.
5. (a) P. J. Kersten, B. Kalyanaraman, K. E. Hammel, B. Reinhammar and T. K. Kirk, Biochem. J., 1990, 268, 475-480;
6. (b) F. Xu, W. Shin, S. H. Brown, J. A. Wahleithner, U. M. Sundaram and E. I. Solomon, Biochim. Biophys. Acta, 1996, 1292, 303-311;
7. K. Li, F. Xu and K.-E. L. Eriksson, Appl. Environ. Microbiol., 1999, 65, 2654-2660.
8. F. Xu, J. J. Kulys, K. Duke, K. L. K. Krikstopaitis, H.-J. W. Deussen, E. Abbate, V. Galinyte and P. Schneider, Appl. Environ. Microbiol., 2000, 66, 2052-2056.
9. F. Xu, Biochemistry, 1996, 35, 7608-7614.
10. (a) R. Bourbonnais and M. G. Paice, FEBS Lett., 1990, 267, 99-102;
11. (b) R. Bourbonnais, M. G. Paice, B. Freiermuth, E. Bodie and S. Borneman, Appl. Environ. Microbiol., 1997, 63, 4627-4632;
12. (c) H.-P. Call and I. Mücke, J. Biotechnol., 1997, 53, 163-202;
13. (d) J. Sealey and A. J. Ragauskas, Enzyme Microb. Technol., 1998, 23, 422-426;
14. (e) M. Fabbrini, C. Galli and P. Gentili, J. Mol. Catal. B: Enzym., 2002, 16, 231-240.
15. P. Baiocco, A. M. Barreca, M. Fabbrini, C. Galli and P. Gentili, Org. Biomol. Chem., 2003, 1, 191-197.
16. H.-J. W. Deussen and C. Johansen, PCT International patent WO 00204 A1, European Patent Office, Munich, Germany, 2000.
17. (a) A. Potthast, T. Rosenau, C. L. Chen and J. S. Gratzl, J. Org. Chem., 1995, 60, 4320-4321;
18. (b) E. Fritz-Langhals and B. Kunath, Tetrahedron Lett., 1998, 39, 5955-5956;
19. (c) A. Majcherczyk, C. Johannes and A. Hüttermann, Appl. Microbiol. Biotechnol., 1999, 51, 267-276;
20. (d) C. Johannes and A. Majcherczyk, Appl. Environ. Microb., 2000, 66, 524-528;
21. (e) C.-L. Chen, A. Potthast, T. Rosenau, J. S. Gratzl, A. G. Kirkman, D. Nagai and T. Miyakoshi, J. Mol. Catal. B: Enzym., 2000, 8, 213-219;
22. (f) M. Fabbrini, C. Galli, P. Gentili and D. Macchitella, Tetrahedron Lett., 2001, 42, 7551-7553.
23. L. Gianfreda, F. Xu and J.-M. Bollag, Bioremed. J., 1999, 3, 1-25.
24. (a) R. Bourbonnais and M. G. Paice, Appl. Microbiol. Biotechnol., 1992, 36, 823-827;
25. (b) E. Srebotnik and K. Hammel, J. Biotechnol., 2000, 81, 179-188.
26. F. d'Acunzo, P. Baiocco, M. Fabbrini, C. Galli and P. Gentili, Eur. J. Org. Chem., 2002, 4195-4201.
27. (a) K. Li, R. F. Helm and K.-E. L. Eriksson, Biotechnol. Appl. Biochem., 1998, 27, 239-243;
28. (b) J. Sealey, A. J. Ragauskas and T. J. Elder, Holzforschung, 1999, 53, 498-502;
29. (c) M. Fabbrini, C. Galli and P. Gentili, J. Mol. Catal. B: Enzym., 2002, 18, 169-171;
30. (d) F. d'Acunzo, P. Baiocco, M. Fabbrini, C. Galli and P. Gentili, New J. Chem., 2002, 26, 1791-1794; A. I. R. P. Castro, D. V. Evtuguin and A. M. B. Xavier, J. Mol. Catal. B: Enzym., 2003, 22, 13-20.
31. (d) F. d'Acunzo, P. Baiocco, M. Fabbrini, C. Galli and P. Gentili, New J. Chem., 2002, 26, 1791-1794; A. I. R. P. Castro, D. V. Evtuguin and A. M. B. Xavier, J. Mol. Catal. B: Enzym., 2003, 22, 13-20.
32. W. Lenk and M. Riedel, J. Phys. Org. Chem., 1990, 3, 687-693.
33. F. Xu, H.-J. W. Deussen, B. Lopez, L. Lam and K. Li, Eur. J. Biochem., 2001, 268, 4168-4176.
34. J. Kulys, H.-J. Deussen, K. Krikstopaitis, R. Lolck, P. Schneider and A. Ziemys, Eur. J. Org. Chem., 2001, 3475-3483.
35. (a) R. Bourbonnais, D. Leech and M. G. Paice, Biochim. Biophys. Acta, 1998, 1379, 381-390;
36. (b) K. Krikstopaitis and J. Kulys, Electrochem. Commun., 2000, 2, 119-123.
37. A. E. J. de Nooy, A. C. Besemer and H. van Bekkum, Synthesis, 1996, 1153-1174.
38. P. Carloni, E. Damiani, L. Greci, P. Stipa, G. Marrosu, R. Petrucci and A. Trazza, Tetrahedron, 1996, 52, 11 257-11 264.
39. K. Piontek, M. Antorini and T. Choinowski, J. Biol. Chem., 2002, 277, 37 663-37 669.
40. R. Amorati, M. Lucarini, V. Mugnaini, G. F. Pedulli, F. Minisci, F. Recupero, F. Fontana, P. Astolfi and L. Greci, J. Org. Chem., 2003, 68, 1747-1754.
41. F. Minisci, C. Punta, F. Recupero, F. Fontana and G. F. Pedulli, Chem. Commun., 2002, 688-689.
42. F. Minisci, C. Punta, F. Recupero, F. Fontana and G. F. Pedulli, J. Org. Chem., 2002, 67, 2671-2676.
43. G. Cantarella, C. Galli and P. Gentili, J. Mol. Catal. B: Enzym., 2003, 22, 135-144.
44. G. Cantarella, F. d'Acunzo and C. Galli, Biotechnol. Bioeng., 2003, 82, 395-398.
45. E. Baciocchi, F. d'Acunzo, C. Galli and O. Lanzalunga, J. Chem. Soc., Perkin Trans. 2, 1996, 133-140.
46. E. Baciocchi, S. Belvedere, M. Bietti and O. Lanzalunga, Eur. J. Org. Chem., 1998, 299-302.
47. D. Rochefort, R. Bourbonnais, D. Leech and M. G. Paice, Chem. Commun., 2003, 1182-1183.
48. G. V. B. Reddy, M. Sridhar and M. H. Gold, Eur. J. Biochem., 2003, 270, 284-292.
49. T. H. Lowry and K. S. Richardson, Mechanism and Theory in Organic Chemistry, 2nd edn., Harper & Row, New York, 1981.
50. E. Baciocchi, M. Bietti and O. Lanzalunga, Acc. Chem. Res., 2000, 33, 243-251.
51. (a) A. M. Barreca, M. Fabbrini, C. Galli, P. Gentili and S. Ljunggren, J. Mol. Catal. B: Enzym., 2003, 26, 105-110;
52. (b) A. M. Barreca, B. Sjögren, M. Fabbrini, C. Galli and P. Gentili, Biocatal. Biotransform. in press.
53. (a) M. J. Jetten, M. T. R. van den Dool, W. van Hartingsveldt and R. T. M. van Wandelen, Patent WO0050621 A2;
54. (b) A. Isogai and Y. Kato, Cellulose, 1998, 5, 153-164.
55. V. Crescenzi, A. Francescangeli, D. Renier and D. Bellini, Macromolecules, 2001, 34, 6367-6372.
56. E. Baciocchi, M. Fabbrini, O. Lanzalunga, L. Manduchi and G. Pochetti, Eur. J. Biochem., 2001, 268, 665-672.
57. P. W. Oxley, B. M. Adger, M. J. Sasse and M. A. Forth, Org. Synth., Coll. Vol. VIII, 1993, 16-19.
58. B. S. Wolfenden and R. L. Willson, J. Chem. Soc., Perkin Trans. 2, 1982, 805-812.