Free radical versus electron-transfer routes of oxidation of hydrocarbons by laccase/mediator systems: Catalytic or stoichiometric procedures

Journal of Molecular Catalysis B: Enzymatic

Volumn 22, Issue 3-4, 2003, Pages 135-144

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

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Electron transfer; H atom abstraction; Hydrocarbons oxidation; Laccase; Lignin degradation; Mediators

Indexed keywords

CHEMICAL BONDS; ELECTRON TRANSPORT PROPERTIES; ENZYMES; OXIDATION; STOICHIOMETRY;

OXIDATION POTENTIAL;

HYDROCARBONS;

FREE RADICAL; LACCASE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; ENZYME SUBSTRATE; HYDROGEN BOND; OXIDATION; OXIDATION REDUCTION POTENTIAL; STOICHIOMETRY; THERMAL ANALYSIS;

EID: 0038244799     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1177(03)00014-6     Document Type: Article

References (51)

1. Labinger J.A., Bercaw J.E. Nature. 417:2002;507-514.
2. Y. Sawaki, Epoxidation and hydroxylation, in: S. Patai (Ed.), The Chemistry of Hydroxyl, Ether and Peroxide Groups, Suppl. E2, Wiley/Interscience, New York, 1993 (Chapter 11).
3. Sono M., Roach M.P., Coulter E.D., Dawson J.H. Chem. Rev. 96:1996;2841-2887.
4. ten Have R., Teunissen P.J.M. Chem. Rev. 101:2001;3397-3413.
5. A. Messerschmidt, Multi-Copper Oxidases, World Scientific, Singapore, 1997.
6. Kersten P.J., Kalyanaraman B., Hammel K.E., Reinhammar B., Kirk T.K. Biochem. J. 268:1990;475-480.
7. Bourbonnais R., Paice M.G. FEBS Lett. 267:1990;99-102.
8. Bourbonnais R., Paice M.G. Appl. Microbiol. Biotechnol. 36:1992;823-827.
9. Bourbonnais R., Paice M.G., Freiermuth B., Bodie E., Borneman S. Appl. Environ. Microb. 63:1997;4627-4632.
10. Crestini C., Argyropoulos D.S. Bioorg. Med. Chem. 6:1998;2161-2169.
11. Fabbrini M., Galli C., Gentili P., Macchitella D. Tetrahedron Lett. 42:2001;7551-7553.
12. Fabbrini M., Galli C., Gentili P. J. Mol. Catal. B: Enzym. 16:2002;231-240. (and work in progress).
13. Potthast A., Rosenau T., Chen C.-L., Gratzl J.S. J. Org. Chem. 60:1995;4320-4321.
14. Fritz-Langhals E., Kunath B. Tetrahedron Lett. 39:1998;5955-5956.
15. Johannes C., Majcherczyk A. Appl. Environ. Microb. 66:2000;524-528.
16. B.S. Wolfenden, R.L. Willson, J. Chem. Soc., Perkin Trans. 2, (1982) 805-812.
17. Oxley P.W., Adger B.M., Sasse M.J., Forth M.A. Org. Synth. Coll. 8:1993;16-19.
18. Xu F., Kulys J.J., Duke K., L K., Krikstopaitis K., Deussen H.-J.W., Abbate E., Galinyte V., Schneider P. Appl. Environ. Microbiol. 66:2000;2052-2056.
19. Xu F., Deussen H.-J.W., Lopez B., Lam L., Li K. Eur. J. Biochem. 268:2001;4169-4176.
20. Majcherczyk A., Johannes C., Hüttermann A. Appl. Microbiol. Biotechnol. 51:1999;267-276.
21. Muheim A., Fiechter A., Harvey P.J., Schoemaker H.E. Holzforschung. 46:1992;121-126.
22. Potthast A., Rosenau T., Fischer K. Holzforschung. 55:2001;47-56.
23. Bourbonnais R., Leech D., Paice M.G. Biochim. Biophys. Acta. 1379:1998;381-390.
24. Fabbrini M., Galli C., Gentili P. J. Mol. Catal. B: Enzym. 18:2002;169-171.
25. Brackman W., Gaasbeek C.J. Recl. Trav. Chim. Pays-Bas. 85:1965;257-267.
26. Eggert C., Temp U., Dean J.F.D., Eriksson K.-E.L. FEBS Lett. 391:1996;144-148.
27. G. Cantarella, F. d'Acunzo, C. Galli, Biotechnol. Bioeng., in press.
28. Iwahama T., Yoshino Y., Keitoku T., Sakaguchi S., Ishii Y. J. Org. Chem. 65:2000;6502-6507.
29. Xu F. J. Biol. Chem. 272:1997;924-928.
30. Majcherczyk A., Johannes C., Hüttermann A. Appl. Microbiol. Biotech. 51:1999;267-276.
31. d'Acunzo F., Baiocco P., Fabbrini M., Galli C., Gentili P. New J. Chem. 26:2002;1791-1794.
32. Li K., Helm R.F., Eriksson K.-E.L. Biotechnol. Appl. Biochem. 27:1998;239-243.
33. F. Minisci, C. Punta, F. Recupero, F. Fontana, G.F. Pedulli, Chem. Commun. (2002) 688-689.
34. McMillen D.F., Golden D.M. Hydrocarbon bond dissociation energies. Annu. Rev. Phys. Chem. 33:1982;493-532.
35. E. Baciocchi, F. d'Acunzo, C. Galli, O. Lanzalunga, J. Chem. Soc. Perkin Trans. 2, (1996) 133-140.
36. Xu F., Shin W., Brown S.H., Wahleithner J.A., Sundaram U.M., Solomon E.I. Biochim. Biophys. Acta. 1292:1996;303-311.
37. Li K., Xu F., Eriksson K.-E.L. Appl. Environ. Microbiol. 65:1999;2654-2660.
38. Xu F., Berka R.M., Wahleithner J.A., Nelson B.A., Shuster J.R., Brown S.H., Palmer A.E., Solomon E.I. Biochem. J. 334:1998;63-70.
39. Baciocchi E., Bietti M., Mattioli M. J. Org. Chem. 58:1993;7106-7110.
40. Howell J., Goncalves J.M., Amatore C., Klasinc L., Wightman R.M., Kochi J.K. J. Am. Chem. Soc. 106:1984;3968-3976.
41. Kersten P.J., Kalyanaraman B., Hammel K.E., Reinhammar B., Kirk T.K. Biochem. J. 268:1990;475-480.
42. Janata J., Williams M.B. J. Phys. Chem. 76:1972;1178-1183.
43. Minisci F., Punta C., Recupero F., Fontana F., Pedulli G.F. J. Org. Chem. 67:2002;2671-2676.
44. Lenk W., Riedl M. J. Phys. Org. Chem. 3:1990;687-693.
45. Greci L. Tetrahedron. 39:1983;677-681.
46. Aurich H.G., Weiss W. Chem. Ber. 106:1973;2408-2414.
47. F. d'Acunzo, C. Galli, in press.
48. Jensen K.A., Bao W., Kawai S., Srebotnik E., Hammel K.E. Appl. Environ. Microbiol. 62:1996;3679-3686.
49. Kapich A.N., Hofrichter M., Vares T., Hatakka A. Biochem. Biophys. Res. Commun. 259:1999;212-219.
50. Kapich A.N., Jensen K.A., Hammel K.E. FEBS Lett. 461:1999;115-119.
51. Böhmer S., Messner K., Srebotnik E. Biochem. Biophys. Res. Commun. 244:1998;233-238.