Evidence consistent with the requirement of cresolase activity for suicide inactivation of tyrosinase

Tohoku Journal of Experimental Medicine

Volumn 216, Issue 3, 2008, Pages 231-238

  Land, Edward J ^a   Ramsden, Christopher A ^a   Riley, Patrick A ^b,c,e   Stratford, Michael R L ^c,d  

^a KEELE UNIVERSITY   (United Kingdom)

^b Totteridge Institute for Advanced Studies   (United Kingdom)

^c UNIVERSITY OF OXFORD   (United Kingdom)

^d UNIVERSITY OF OXFORD   (United Kingdom)

^e TIFAS   (United Kingdom)

Author keywords

Catechol oxidase; Cresolase; Reductive elimination; Suicide inactivation; Tyrosinase

Indexed keywords

3,6 DIMETHYLCATECHOL; 4 FLUOROCATECHOL; 4 METHOXYCATECHOL; 4 METHYLCATECHOL; CATECHOL; CATECHOL OXIDASE; DOPA; DOPAMINE; MEQUINOL; MONOPHENOL MONOOXYGENASE; PARA CRESOL; PYROGALLOL; TYRAMINE; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; BANANA; CATALYSIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INACTIVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; OXIDATION; OXIMETRY;

AGARICUS; CATALYSIS; CATECHOLS; ENZYME ACTIVATION; KINETICS; MONOPHENOL MONOOXYGENASE; MUSA; OXIDATION-REDUCTION; OXYGEN; RESORCINOLS;

EID: 59849124373     PISSN: 00408727     EISSN: 13493329     Source Type: Journal    
DOI: 10.1620/tjem.216.231     Document Type: Article

References (23)

1. Asimov, I. & Dawson, C.R. (1950) On the reaction inactivation of tyrosinase during aerobic oxidation of catechol. J. Am. Chem. Soc., 72, 820-828.
2. Brown C.R. (1983) Banana polyphenol oxidase. Schools Science Review, 65, 691-695.
3. Cooksey, C.J. Garratt, P.J., Land, E.J., Pavel, S., Ramsden, C.A., Riley, P.A. & Smit, N.P.M. (1997) Evidence of the indirect formation of the catecholic intermediate substrate responsible for the autoactivation kinetics of tyrosinase. J. Biol. Chem., 272, 26226-26235.
4. Corse, J. & Ingraham, L.L. (1951) The monofluorocatechols. J. Org. Chem., 16, 1345-1348.
5. Dietler, C. & Lerch, K. (1982) Reaction inactivation of tyrosinase. In: Oxidases and Related Redox Systems, edited by I.E. King, H.S. Mason & M. Morrison, Pergamon Press, NY, pp. 305-317.
6. Eicken, C., Zippel, F., Büldt-Karentzopoulos, K. & Krebs, B. (1998) Biochemical and spectroscopic characterization of catechol oxidase from sweet potatoes (Ipomoea batatas) containing a type-3 dicopper center. FEBS Lett., 436, 293-299.
7. García-Cánovas, F., Tudela, J., Martínez-Madrid, C., Varón, R., Garcia-Carmona, F. & Lozano, J.A. (1987) Kinetic study on the suicide inactivation of tyrosinase induced by catechol. Biochim. Biophys. Acta, 912, 417-423.
8. Gerdemann, C., Eicken, C. & Krebs, B. (2002) The crystal structure of catechol oxidase: New insight into the function of type-3 copper proteins. Acc. Chem. Res., 35, 183-191.
9. Hughes, A.L. (1999) Evolution of the arthropod prophenoloxidaxe/ hexamerin protein family. Immunogenetics, 49, 106-114.
10. Jolley, R.L. Jr., Nelson, R.M. & Robb, D.A. (1969) The Multiple Forms of Mushroom Tyrosinase. Structural Studies on the Isozymes. J. Biol. Chem., 244, 3251-3257.
11. Klabunde, T., Eicken, C., Sacchettini, J.C. & Krebs, B. (1998) Crystal structure of a plant catechol oxidase containing a dicopper center. Nat. Struct. Biol., 5, 1084-1090.
12. Land, E.J., Ramsden, C.A. Riley, P.A. (2007) The mechanism of suicide-inactivation of tyrosinase: a substrate structure investigation. Tohoku J. Exp. Med., 212, 341-348.
13. Land, E.J., Ramsden, C.A. Riley, P.A. & Stratford, M.R.L. (2008) Studies of para-quinomethano formation during the tyrosinase-catalysed oxidation of 4-alkylcatechols. Arkivoc, 2008, (ii), 258-267.
14. Mason, H.S. (1955) Comparative biochemistry of the phenolase complex. In: Advances in Enzymology, vol. 16, edited by F.F. Nord, Interscience Publishers Inc., NY, pp. 105-184.
15. Mason, H.S., Fowlks, W.L. & Peterson, E. (1955) Oxygen transfer and electron transport by the phenolase complex. J. Am. Chem. Soc., 77, 2914-2915.
16. Matoba, Y., Kumagai, T., Yamamoto, A., Yoshitsu, H. & Sugiyama, M. (2006) Crystallographic evidence that dinuclear copper center of tyrosinase is flexible during catalysis. J. Biol. Chem., 281, 8981-8990.
17. Mayer, A.M. & Harel, E. (1979) Polyphenol oxidases in plants. Phytochemistry, 18, 193-215.
18. Pomerantz, S.H. (1966) The tyrosine hydroxylase activity of mammalian tyrosinase. J. Biol. Chem., 241, 161-168.
19. Seiji, M., Sasaki M. & Tomita, Y. (1978) Nature of tyrosinase inactivation in melanosomes. Tohoku J. Exp. Med., 125, 233-245.
20. Tomita, Y., Hariu, A., Mizuno, C. & Seiji, M. (1980) Inactivation of tyrosinase by dopa. J. Invest. Dermatol., 75, 379-382.
21. Tudela, J., Garcia-Cánovas, F., Varón, R., Jiménez, M., García-Carmona, F. & Lozano, J.A. (1988) Kinetic study in the transient phase of the suicide inactivation of frog epidermis tyrosinase. Biophys. Chem., 30, 303-310.
22. Walker, J.R. & Ferrar, P.H. (1998) Diphenol oxidases, enzyme-catalysed browning and plant disease resistance. Biotechnol. Genet. Eng. Rev., 15, 457-498.
23. Yang, C.P., Fujita, S., Ashrafuzzaman, M., Nakamura, N. & Hayashi, N. (2000) Purification and characterization of polyphenol oxidase from banana (Musa sapientum L.) pulp. J. Agric. Food Chem., 48, 2732-2735.