Tyrosinase: The four oxidation states of the active site and their relevance to enzymatic activation, oxidation and inactivation

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 8, 2014, Pages 2388-2395

  Ramsden, Christopher A ^a   Riley, Patrick A ^b  

^a KEELE UNIVERSITY   (United Kingdom)

^b Totteridge Institute for Advanced Studies   (United Kingdom)

Author keywords

Melanin; Monooxygenase; Oxidase; Quinones; Tyrosinase

Indexed keywords

MONOPHENOL MONOOXYGENASE; CATECHOL; CATECHOL DERIVATIVE; QUINONE DERIVATIVE; RESORCINOL DERIVATIVE;

ANTIBIOSIS; BACILLUS MEGATERIUM; BACILLUS THURINGIENSIS; BACTERIAL STRAIN; BIOTRANSFORMATION; CATALYSIS; ENZYME ACTIVATION; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME CONFORMATION; ENZYME INACTIVATION; ENZYME ISOLATION; ENZYME KINETICS; ENZYME METABOLISM; MELANOGENESIS; MOLECULAR EVOLUTION; NONHUMAN; OXIDATION REDUCTION POTENTIAL; OXYGENATION; PSEUDOMONAS PUTIDA; REVIEW; SIGNAL TRANSDUCTION; STREPTOMYCES; STREPTOMYCES CASTANGLOBISPORUS; STREPTOMYCES GLAUCESCENS; STREPTOMYCES NIGRIFACIENS; TAUTOMER; THERMOMICROBIUM ROSEUM; VIBRIO; VIBRIO TYROSINATICUS; X RAY CRYSTALLOGRAPHY; CHEMISTRY; KINETICS; METABOLISM; OXIDATION REDUCTION REACTION;

CATALYTIC DOMAIN; CATECHOLS; KINETICS; MONOPHENOL MONOOXYGENASE; OXIDATION-REDUCTION; QUINONES; RESORCINOLS;

EID: 84897972480     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.02.048     Document Type: Review

References (74)

1. Riley, P. A.; Ramsden, C. A.; Land, E. J. In Melanins and Melanosomes: Biosynthesis, Biogenesis, Physiological and Pathological Functions; Borovansky, J., Riley, P. A., Eds.; Wiley-VCH Verlag GmbH & Co.: Weinheim, 2011; pp. 63.
2. H.S. Raper Physiol. Revs. 8 1928 245
3. S. Ito, and K. Wakamatsu Photochem. Photobiol. 84 2008 582
4. R.A. Wogelius, P.L. Manning, H.E. Barden, N.P. Edwards, S.M. Webb, W.I. Sellers, K.G. Taylor, P.L. Larson, P. Dodson, H. You, L. Da-qing, and U. Bergmann Science 333 2011 1622
5. E.A. Lewis, and W.B. Tolman Chem. Rev. 104 2004 1047
6. H. Claus, and H. Decker Syst. Appl. Microbiol. 29 2006 3
7. J.M. Nelson, and C.R. Dawson Adv. Enzymol. 4 1944 99
8. A.B. Lerner, T.B. Fitzpatrick, E. Calkins, and W.H. Summerson J. Biol. Chem. 187 1950 793
9. M. Fling, N.H. Horowitz, and S.F. Heinemann J. Biol. Chem. 238 1963 2045
10. R.L. Jolley, L.H. Evans, N. Makino, and H.S. Mason J. Biol. Chem. 249 1974 335
11. C.W.G. van Gelder, W.H. Flurkey, and H.J. Wichers Phytochemistry 45 1997 1309
12. K.-H. Kong, M.-P. Hong, S.-S. Choi, Y.-T. Kim, and S.-H. Cho Biotechnol. Appl. Biochem. 31 2000 113
13. N. Liu, T. Zhang, Y.J. Wang, Y.P. Huang, J.H. Ou, and P. Shen Lett. Appl. Microbiol. 39 2004 407
14. A.M. McMahon, E.M. Doyle, S. Brooks, and K.E. O'Connor Enzyme Microb. Technol. 40 2007 1435
15. M. Sendovski, M. Kanteev, V.S. Ben-Yosef, N. Adir, and A. Fishman J. Mol. Biol. 405 2011 227
16. Y. Matoba, T. Kumagai, A. Yamamoto, H. Yoshitsu, and M. Sugiyama J. Biol. Chem. 281 2006 8981
17. K.G. Strothkamp, R.L. Jolley, and H.S. Mason Biochem. Biophys. Res. Commun. 70 1976 519
18. W.T. Ismaya, H.J. Rozeboom, A. Weijn, J.J. Mes, F. Fusetti, H.J. Wichers, and B.W. Dijkstra Biochemistry 50 2011 5477
19. J.C. Espin, R. Varón, L.G. Fenoll, M.A. Gilabert, P.A. Garcia-Ruíz, J. Tudela, and F. Garcia-Cánovas Eur. J. Biochem. 267 2000 1270
20. W.H. Flurkey, and J.K. Inlow J. Inorg. Biochem. 102 2008 2160
21. T. Klabunde, C. Eicken, J.C. Sacchettini, and B. Krebs Nature Struct. Biol. 5 1998 1084
22. V.M. Virador, J.P. Reyes-Grajeda, A. Blanco-Labra, E. Mendiola-Olaya, G.M. Smith, A. Moreno, and J.R. Whitaker Agric. Food Chem. 58 2010 1189
23. W.P.J. Gaykema, W.G.J. Hol, J.M. Vereijken, N.M. Soeter, H.J. Bak, and J.J. Beintema Nature (London) 309 1984 23
24. B. Hazes, K.A. Magnus, C. Bonaventura, J. Bonaventura, Z. Dauter, K.H. Kalk, and W.G.J. Hol Protein Sci. 2 1993 597
25. M.E. Cuff, K.I. Miller, K.E. van Holde, and W.A.J. Hendrickson Mol Biol. 278 1998 855
26. Y. Li, Y. Wang, H. Jiang, and J. Deng Proc. Natl. Acad. Sci. U.S.A. 106 2009 17002
27. S.D. Longa, I. Ascone, A. Bianconi, A. Bonfigli, A.C. Castellano, O. Zarivi, and M. Miranda J. Biol. Chem. 271 1996 21025
28. H. Decker, and F. Tuczek Trends Biochem. Sci. 25 2000 392
29. H. Decker, T. Schweikardt, and F. Tuczek Angew. Chem., Int. Ed. 45 2006 4546
30. H. Decker, T. Schweikardt, D. Nillius, U. Salzbrunn, E. Jaenicke, and F. Tuczek Gene 398 2007 183
31. C. Olivares, J.C. Garcia-Borrón, and F. Solano Biochemistry 41 2002 679
32. C. Citek, C.T. Lyons, E.C. Wasinger, and T.D.P. Stack Nature Chem. 4 2012 317
33. N. Fujieda, S. Yabuta, T. Ikeda, T. Oyama, N. Muraki, G. Kurisu, and S. Itoh J. Biol. Chem. 288 2013 22128
34. Borovansky, J.; Riley, P. A. In Melanins and Melanosomes: Biosynthesis, Biogenesis, Physiological and Pathological Functions; Borovansky, J., Riley, P. A., Eds.; Wiley-VCH Verlag GmbH & Co.: Weinheim, 2011, pp. 343-381.
35. D. Hernández-Romero, A. Sanchez-Amat, and F. Solano FEBS J. 273 2006 257
36. Lerch, K. In Metal Ions in Biological Systems. Vol. 13: Copper Proteins; Sigel, H., Ed.; Marcel-Dekker: New York: 1981, 143.
37. N. Makino, and H.S. Mason J. Biol. Chem. 248 1973 5731
38. J.R. Ros, J.N. Rodriguez-López, and F. Garcia-Cánovas Biochem. J. 295 1993 309
39. A. Palumbo, G. Misuraca, M. d'Ischia, and G. Prota Biochem. J. 228 1985 647
40. A. Palumbo, M. d'Ischia, G. Misuraca, L. Carratú, and G. Prota Biochem. Biophys. Acta 1033 1990 256
41. E.J. Land, C.A. Ramsden, and P.A. Riley Arkivoc xi 2007 23
42. W.C. Evans, and H.S. Raper Biochem. J. 31 1937 2162
43. E.J. Land, C.A. Ramsden, and P.A. Riley Acc. Chem. Res. 36 2003 300
44. A. Thompson, E.J. Land, M.R. Chedekel, K.V. Subbarao, and T.G. Truscott Biochim. Biophys. Acta 843 1985 49
45. E.J. Land, and P.A. Riley Pigment Cell Res. 13 2000 273
46. E.J. Land, S. Ito, K. Wakamatsu, and P.A. Riley Pigment Cell Res. 16 2003 487
47. P.A. Riley Cell Mol. Biol. 45 1999 951
48. C.J. Cooksey, P.J. Garratt, E.J. Land, S. Pavel, C.A. Ramsden, P.A. Riley, and N.P.M. Smit J. Biol. Chem. 272 1997 26226
49. J. Clews, C.J. Cooksey, P.J. Garratt, E.J. Land, C.A. Ramsden, and P.A. Riley J. Chem. Soc., Chem. Commun. 1998 77
50. S. Naish-Byfield, C.J. Cooksey, and P.A. Riley Biochem. J. 304 1994 155
51. C.J. Cooksey, E.J. Land, F.A.P. Rushton, C.A. Ramsden, and P.A. Riley Quant. Struct.-Act. Relat. 15 1996 498
52. C.J. Cooksey, E.J. Land, C.A. Ramsden, and P.A. Riley Anti-Cancer Drug Design 10 1995 119
53. S. Naish-Byfield, and P.A. Riley Pigment Cell Res. 11 1998 127
54. S. Naish-Byfield, and P.A. Riley Biochem. J. 288 1992 63
55. C.J. Cooksey, P.J. Garratt, E.J. Land, C.A. Ramsden, and P.A. Riley Biochem. J. 333 1998 685
56. S. Naish-Byfield, C.J. Cooksey, A.M. Latter, C. Johnson, and P.A. Riley Melanoma Res. 1 1991 273
57. S. Naish-Byfield, and P.A. Riley Pigment Cell Res. 11 1998 94
58. M. Seiji, and T.B. Fitzpatrick J. Biochem. 49 1961 700
59. Y. Tomita, A. Hariu, C. Mizuno, and M.J. Seiji Invest. Derm. 75 1980 379
60. M. Seiji, M. Sasaki, and Y. Tomita Tohoku J. Exp. Med. 125 1978 233
61. K. Shimao, M. Seiji, and H. Fukuzawa Tohoku J. Exp. Med. 114 1974 263
62. Y. Tomita, M. Seiji, and A. Igarashi J. Dermatol. 7 1980 377
63. E.J. Land, C.A. Ramsden, and P.A. Riley Tohoku J. Exp. Med. 212 2007 341
64. Dietler, C.; Lerch, K. In Oxidases and Related Redox Systems, King, T. E., Mason, H. S., Morrison M., Eds.; Pergamon Press: New York, 1982: pp 305.
65. C.A. Ramsden, M.R.L. Stratford, and P.A. Riley Org. Biomol. Chem. 7 2009 3388
66. E.J. Land, C.A. Ramsden, P.A. Riley, and M.R.L. Stratford Tohoku J. Exp. Med. 216 2008 231
67. C.A. Ramsden, and P.A. Riley Arkivoc x 2010 248
68. C.A. Ramsden, and P.A. Riley Arkivoc i 2010 260
69. M.R.L. Stratford, C.A. Ramsden, and P.A. Riley Bioorg. Med. Chem. 21 2013 1166
70. M.R.L. Stratford, C.A. Ramsden, and P.A. Riley Bioorg. Med. Chem. 20 2012 4364
71. P.A. Riley J. Theor. Biol. 203 2000 1
72. H.S. Mason Adv. Enzymol. 16 1955 105
73. S.H. Pomerantz J. Biol. Chem. 241 1966 161
74. S. Jawaid, T.H. Khan, H.M.I. Osborn, and N.A.O. Williams Anticancer Agents Med. Chem. 9 2009 717