Deuterium isotope effect on the oxidation of monophenols and o-disphenols by tyrosinase

Biochemical Journal

Volumn 380, Issue 3, 2004, Pages 643-650

  Fenoll, Lorena G ^a   Peñalver, María José ^a   Rodríguez López, José N ^a   Garcia Ruiz P A ^a   García Cánovas, Francisco ^a   Tudela, José ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

Deuterium isotope effect; Diphenols; Monophenols; Mushroom; Polyphenol oxidase; Tyrosinase

Indexed keywords

CATALYSTS; DEUTERIUM; ISOTOPES; OXIDATION; PROTONS; SOLVENTS; SUBSTRATES;

CATALYTIC CONSTANT; KINETIC PARAMETER; MOLAR FRACTION; SUBSTRATE BINDING;

PHENOLS;

CATECHOL OXIDASE; DEUTERIUM; MONOPHENOL MONOOXYGENASE; TYROSINE;

ARTICLE; CATALYSIS; ELECTRON TRANSPORT; ENZYME ACTIVITY; ENZYME DEGRADATION; ENZYME KINETICS; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; OXIDATION KINETICS; PRIORITY JOURNAL; PROTEIN ANALYSIS;

AGARICALES; DEUTERIUM; FUNGAL PROTEINS; ISOTOPES; MONOPHENOL MONOOXYGENASE; OXIDATION-REDUCTION; PHENOLS;

BASIDIOMYCOTA;

EID: 3042704061     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/BJ20040136     Document Type: Article

References (37)

1. Prota, G., d'Ischia, M. and Napolitano, A. (1998) The chemistry of melanins and related metabolites. In The Pigmentary System, Physiology and Pathology (Nordlund, J. J., Boissy, R. E., Hearing, V. J., King, R. A. and Ortonne, J. P., eds.), pp. 307-332, Oxford University Press, Oxford
2. Nicolas, J. J., Richard-Forget, F., Goupy, P. M., Amiot, M. J. and Aubert, S. (1994) Enzymatic browning reactions in apple products. Crit. Rev. Food Sci. 34, 109-157
3. Zawistowski, J., Biliaderis, C. G. and Eskin, N. A. M. (1991) Polyphenol Oxidase. In Oxidative Enzymes in Foods (Robinson, D. S. and Eskin, N. A. M., eds.), pp. 217-273, Elsevier Science, London
4. Van Gelder, C. W. G. and Flurkey, W. A. J. (1997) Sequence and structural features of plant and fungal tyrosinases. Phytochemistry 45, 1309-1323
5. Mason, H. S. (1956) Structure and functions of the phenolase complex. Nature (London) 177, 79-81
6. Sánchez-Ferrer, A., Rodríguez-López, J. N., García-Cánovas, F. and García-Carmona, F., (1995) Tyrosinase: a comprehensive review of its mechanism. Biochim. Biophys. Acta 1247, 1-11
7. García-Cánovas, F., García-Carmona, F., Vera-Sánchez, J., Iborra, J. L. and Lozano, J. A. (1982) The role of pH in the melanin biosynthesis pathway. J. Biol. Chem. 257, 8738-8744
8. Rodríguez-López, J. N., Tudela, J., Varón, R., García-Carmona, F. and García-Cánovas, F. (1992) Analysis of a kinetic model for melanin biosynthesis pathway. J. Biol. Chem. 267, 3801-3810
9. Yong, G., Leone, O. and Strothkamp, K. G. (1990) Agaricus bisporus metapotyrosinase: preparation, characterization, and conversion to mixed-metal derivatives of the binuclear site. Biochemistry 29, 9684-9690
10. Jolley, Jr, R. L., Evans, L. H., Makino, N. and Mason, H. S. (1974) Oxytyrosinase. J. Biol. Chem. 249, 335-345
11. Solomon, E. I., Sundaram, U. M. and Machonkin, T. E. (1996) Multicopper oxidases and oxygenases. Chem. Rev. 96, 2563-2605
12. Ros, J. R., Rodríguez-López, J. N. and García- Cánovas, F. (1994) Tyrosinase: kinetic analysis of the transient phase and the steady state. Biochim. Biophys. Acta 1204, 33-42
13. Ros, J. R., Rodríguez-López, J. N. and García- Cánovas, F. (1993) Effect of L-ascorbic acid on the monophenolase activity of tyrosinase. Biochem. J. 295, 309-312
14. Espín, J. C., Varon, R., Fenoll, L. G., Gilabert, M. A., García-Ruiz, P. A., Tudela, J. and García-Cánovas, F. (2000) Kinetic characterization of the substrate specificity and mechanism of mushroom tyrosinase. Eur. J. Biochem. 267, 1-11
15. Fenoll, L. G., Rodriguez-Lopez, J. N., García-Sevilla, F., Tudela, J., García-Ruiz, P. A., Varon, R. and García-Cánovas, F. (2000) Oxidation by mushroom tyrosinase of monophenols generating slightly unstable o-quinones. Eur. J. Biochem. 267, 1-15
16. Fenoll, L. G., Rodríguez-López, J. N., García- Sevilla, F., García-Ruiz, P. A., Varón, R., García- Cánovas, F. and Tudela, J. (2001) Analysis and interpretation of the action mechanism of mushroom tyrosinase on monophenols and diphenols generating highly unstable o-quinones. Biochim. Biophys. Acta 1548, 1-22
17. Rodriguez-Lopez, J. N., Fenoll, L. G., García-Ruiz, P. A., Varon, R., Tudela, J., Thorneley, R. N. and García-Cánovas, F. (2000) Stopped-flow and steady-state study of the diphenolase activity of mushroom tyrosinase. Biochemistry 39, 10497-10506
18. Conrad, J. S., Dawson, S. R., Hubbard, E. R., Meyers, T. E. and Strothkamp, K. G. (1994) Inhibitor binding to the binuclear active site of tyrosinase: temperature, pH, and solvent deuterium isotope effects. Biochemistry 33, 5739-5744
19. Venkatasuban, K. S. and Schowen, R. L. (1984) The proton inventory technique. Crit. Rev. Biochem. 17, 1-44
20. Peñalver, M. J., Rodríguez-López, J. N., García-Ruiz, P. A., García-Cánovas, F. and Tudela, J. (2003) Solvent deuterium isotope effect on the oxidation of o-diphenols by tyrosinase. Biochim. Biophys. Acta 1650, 128-135
21. Rodríguez-López, J. N., Escribano, J. and García-Cánovas, F. (1994) A continuous spectrophotometric method for the determination of monophenolase activity of tyrosinase using 3-methyl-2-benzothializone hydrazone. Anal. Biochem. 216, 205-212
22. Espin, J. C., García-Ruiz, P. A., Tudela, J. and García-Cánovas, F. (1998) Study of the stereospecificity in mushroom tyrosinase. Biochem. J. 331, 547-551
23. Duckworth, H. W. and Coleman, J. E. (1970) Physicochemical and kinetic properties of mushroom tyrosinase. J. Biol. Chem. 245 1613-1625
24. Bradford, M. M. (1976) A rapid and sensitive method for the quantification of microgram quantities of proteins utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-256
25. Winder, A. J. and Harris, H. (1991) New assays for the tyrosine hydroxylase and dopa oxidase activities of tyrosinase. Eur. J. Biochem. 198, 317-326
26. Espín, J. C., Morales, M., Varón, R., Tudela, J. and García-Cánovas, F. (1996) A continuous spectrophotometric method for determining the monophenolase and diphenolase activities of pear polyphenol oxidase. J. Food Sci. 61, 1177-1201
27. Ros, J. R., Rodríguez-López, J. N., Varón, R. and García-Cánovas, F. (1994) Kinetics study of the oxidation of 4-tert-butylphenol by tyrosinase. Eur. J. Biochem. 222, 449-452
28. Draper, N. R. and Smith, H. (1981) Applied Regression Analysis, Wiley, New York
29. Endrenyi, L. (1981) Kinetic Data Analysis: Design and Analysis of Enzyme and Pharmacokinetics Experiments, Plenum Press, New York
30. Marquardt, D. W. (1963) An algorithm for least-squares estimation of non-linear parameters. J. Soc. Ind. Appl. Math. 11, 431-441
31. Reference deleted
32. Schowen, K. B. and Schowen, R. L. (1982) Solvent isotope effects on enzyme systems. Methods Enzymol. 87, 551-606
33. Schowen, R. L. (1977) In Isotope Effects on Enzyme-Catalyzed Reactions (Cleland, W. W., O'Leary, M. H. and Northrop, D. B., eds.), pp. 64-99, University Park Press, Baltimore
34. Albery, J. (1975) In Proton-Transfer Reactions (Caldin, E. and Gold, V., eds.), pp. 263-315, Wiley & Sons, New York
35. Espin, J. C., García-Ruiz, P. A., Tudela, J. and García-Cánovas, F. (1996) Study of stereospecificity in pear and strawberry polyphenol oxidases. J. Food Sci. 46, 2469-2473
36. Fenoll, L. G., Rodríguez-López, J. N., Varón, R., García-Ruiz, P. A., García-Cánovas, F. and Tudela, J. (2000) Action mechanism of tyrosinase on meta- and para-hydroxylated monophenols. Biol. Chem. 381, 313-320
37. Eisenstein, O., Geissner-Prettre, C., Maddaluno, J., Stussi, D. and Weber, J. (1992) Theoretical study of oxyhemocyanin active site: a possible insight on the first step of phenol oxidation of tyrosinase. Arch. Biochem. Biophys. 296, 247-255