Bacterial tyrosinases and their applications

Process Biochemistry

Volumn 47, Issue 12, 2012, Pages 1749-1760

  Faccio, Greta ^a,b   Kruus, Kristiina ^b   Saloheimo, Markku ^b   Thöny Meyer, Linda ^a  

^a SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

^b VTT TECHNICAL RESEARCH CENTRE OF FINLAND   (Finland)

Author keywords

Bioremediation; Biosensors; Biosynthesis; Dyeing; Food; Tyrosinase

Indexed keywords

ACTINOBACTERIA; AMINO GROUP; CAFFEIC ACIDS; CONCOMITANT REDUCTION; DYEING AGENTS; ENVIRONMENTAL STRESS; FUNCTIONALISATION; PHENOLIC COMPOUNDS; PHYSICOCHEMICAL PROPERTY; PROTEOBACTERIA; SUBSTRATE SPECIFICITY; TYROSINASE;

AMINO ACIDS; BIOCHEMISTRY; BIOREMEDIATION; BIOSENSORS; BIOSYNTHESIS; CHEMICAL COMPOUNDS; CHEMICAL PROPERTIES; DYEING; FOOD PROCESSING; FOOD PRODUCTS; SUBSTRATES;

PHENOLS;

ACTINOBACTERIA; AGARICUS BISPORUS; BACTERIA (MICROORGANISMS); BASIDIOMYCOTA; PROTEOBACTERIA;

EID: 84870817930     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2012.08.018     Document Type: Review

References (182)

1. P.M. Plonka, and M. Grabacka Melanin synthesis in microorganisms - biotechnological and medical aspects Acta Biochim Pol 53 2006 429 443
2. J. Geng, S.B. Yu, X. Wan, X.J. Wang, P. Shen, and P. Zhou Protective action of bacterial melanin against DNA damage in full UV spectrums by a sensitive plasmid-based noncellular system J Biochem Biophys Methods 70 2008 1151 1155
3. J. García-Rivera, and A. Casadevall Melanization of Cryptococcus neoformans reduces its susceptibility to the antimicrobial effects of silver nitrate Med Mycol 39 2001 353 357
4. J. Geng, P. Yuan, C. Shao, S.B. Yu, B. Zhou, and P. Zhou Bacterial melanin interacts with double-stranded DNA with high affinity and may inhibit cell metabolism in vivo Arch Microbiol 192 2010 321 329
5. Y. Matoba, T. Kumagai, A. Yamamoto, H. Yoshitsu, and M. Sugiyama Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis J Biol Chem 281 2006 8981 8990
6. M. Sendovski, M. Kanteev, V.S. Ben-Yosef, N. Adir, and A. Fishman First structures of an active bacterial tyrosinase reveal copper plasticity J Mol Biol 405 2011 227 237
7. W.T. Ismaya, H.J. Rozeboom, A. Weijn, J.J. Mes, F. Fusetti, and H.J. Wichers Crystal structure of Agaricus bisporus mushroom tyrosinase: identity of the tetramer subunits and interaction with tropolone Biochemistry 50 2011 5477 5486
8. T. Klabunde, C. Eicken, J.C. Sacchettini, and B. Krebs Crystal structure of a plant catechol oxidase containing a dicopper center Nat Struct Biol 5 1998 1084 1090
9. V.M. Virador, J.P. Reyes Grajeda, A. Blanco-Labra, E. Mendiola-Olaya, G.M. Smith, and A. Moreno Cloning, sequencing, purification, and crystal structure of Grenache (Vitis vinifera) polyphenol oxidase J Agric Food Chem 58 2010 1189 1201
10. N. Malviya, M. Srivastava, S.K. Diwakar, and S.K. Mishra Insights to sequence information of polyphenol oxidase enzyme from different source organisms Appl Biochem Biotechnol 165 2011 397 405
11. H. Claus, and H. Decker Bacterial tyrosinases Syst Appl Microbiol 29 2006 3 14
12. M. Fairhead, and L. Thöny-Meyer Bacterial tyrosinases: old enzymes with new relevance to biotechnology New Biotechnol 29 2012 183 191
13. C. Popa, and G. Bahrim Streptomyces tyrosinase: production and practical applications Innovat Rom Food Biotechnol 8 2011 1 7
14. H.C. Eisenman, and A. Casadevall Synthesis and assembly of fungal melanin Appl Microbiol Biotechnol 93 2012 931 940
15. J.H. Jang, and K.D. Moon Inhibition of polyphenol oxidase and peroxidase activities on fresh-cut apple by simultaneous treatment of ultrasound and ascorbic acid Food Chem 124 2011 444 449
16. J.G. Jee, S.J. Park, and H.J. Kim Tyrosinase-induced cross-linking of tyrosine-containing peptides investigated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry Rapid Commun Mass Spectrom 14 2000 1563 1567
17. T.S. Chang An updated review of tyrosinase inhibitors Int J Mol Sci 10 2009 2440 2475
18. E.I. Solomon, M.J. Baldwin, and M.D. Lowery Electronic structures of active sites in copper proteins: contributions to reactivity Chem Rev 92 1992 521 542
19. A.M. Betancourt, V. Bernan, W. Herber, and E. Katz Analysis of tyrosinase synthesis in Streptomyces antibioticus Microbiology 138 1992 787 794
20. P.Y. Kohashi, T. Kumagai, Y. Matoba, A. Yamamoto, M. Maruyama, and M. Sugiyama An efficient method for the overexpression and purification of active tyrosinase from Streptomyces castaneoglobisporus Protein Exp Purif 34 2004 202 207
21. M. Fairhead, and L. Thöny-Meyer Role of the C-terminal extension in a bacterial tyrosinase FEBS J 277 2010 2083 2095
22. Y. Kawamura-Konishi, S. Maekawa, M. Tsuji, and H. Goto C-terminal processing of tyrosinase is responsible for activation of Pholiota microspora proenzyme Appl Microbiol Biotechnol 90 2010 227 234
23. N. Fujieda, M. Murata, S. Yabuta, T. Ikeda, C. Shimokawa, and Y. Nakamura Multifunctions of MelB, a fungal tyrosinase from Aspergillus oryzae ChemBioChem 13 2012 193 201
24. W.H. Flurkey, and J.K. Inlow Proteolytic processing of polyphenol oxidase from plants and fungi J Inorg Biochem 102 2008 2160 2170
25. A.M. Nambudiri, J.V. Bhat, and P.V. Rao Enzymic conversion of p-coumarate into caffeate by Streptomyces nigrifaciens Biochem J 128 1972 63
26. N. Liu, T. Zhang, Y.J. Wang, Y.P. Huang, J.H. Ou, and P. Shen A heat inducible tyrosinase with distinct properties from Bacillus thuringiensis Lett Appl Microbiol 39 2004 407 412
27. E. Fernandez, A. Sanchez-Amat, and F. Solano Location and catalytic characteristics of a multipotent bacterial polyphenol oxidase Pigment Cell Res 12 1999 331 339
28. M. Beltramini, and K. Lerch Fluorescence properties of Neurospora tyrosinase Biochem J 205 1982 173 180
29. C. Gasparetti, G. Faccio, M. Arvas, J. Buchert, M. Saloheimo, and K. Kruus Discovery of a new tyrosinase-like enzyme family lacking a C-terminally processed domain: production and characterization of an Aspergillus oryzae catechol oxidase Appl Microbiol Biotechnol 86 2010 213 226
30. M.P. Jackman, A. Hajnal, and K. Lerch Albinomutants of Streptomyces glaucescens tyrosinase Biochem J 274 1991 707 713
31. M. Huber, and K. Lerch Identification of two histidines as copper ligands in Streptomyces glaucescens tyrosinase Biochemistry 27 1988 5610 5615
32. C.M. Marusek, N.M. Trobaugh, W.H. Flurkey, and J.K. Inlow Comparative analysis of polyphenol oxidase from plant and fungal species J Inorg Biochem 100 2006 108 123
33. Bustos Arcos VP. Produccion de melaninas en microorganismos recombinantes Mex. Patent MXPA04004786A. 04.05.20; 2005.
34. Stephanopoulos G, Santos CNS. Methods for identifying bacterial strains that produce l-tyrosine. United States Patent Appl US0151496 A1. 09.02.26; 2011.
35. C.N.S. Santos, and G. Stephanopoulos Melanin-based high-throughput screen for l-tyrosine production in Escherichia coli Appl Environ Microbiol 74 2008 1190 1197
36. B.Y.V. Shuster, M. Sendovski, and A. Fishman Directed evolution of tyrosinase for enhanced monophenolase/diphenolase activity ratio Enzyme Microb Technol 47 2010 372 376
37. M.P. Jackman, M. Huber, A. Hajnal, and K. Lerch Stabilization of the oxy form of tyrosinase by a single conservative amino acid substitution Biochem J 282 1992 915 918
38. K.I. Miller, M.E. Cuff, W.F. Lang, P. Varga-Weisz, K.G. Field, and K.E. van Holde Sequence of the Octopus dofleini hemocyanin subunit: structural and evolutionary implications J Mol Biol 278 1998 827 842
39. J.N. Rodríguez-López, L.G. Fenoll, P.A. García-Ruiz, R. Varón, J. Tudela, and R.N. Thorneley Stopped-flow and steady-state study of the diphenolase activity of mushroom tyrosinase Biochemistry 39 2000 10497 10506
40. S. Hirota, T. Kawahara, E. Lonardi, E. de Waal, N. Funasaki, and G.W. Canters Oxygen binding to tyrosinase from Streptomyces antibioticus studied by laser flash photolysis J Am Chem Soc 127 2005 17966 17967
41. L.L. Liaw, and Y.H. Lee Histidine residues 102 and 117 of MelC1 play different roles in the chaperone function for Streptomyces apotyrosinase Biochem Biophys Res Commun 214 1995 447 453
42. D. Lopez-Serrano, F. Solano, and A. Sanchez-Amat Identification of an operon involved in tyrosinase activity and melanin synthesis in Marinomonas mediterranea Gene 342 2004 179 187
43. D. Hernández-Romero, A. Sanchez-Amat, and F. Solano A tyrosinase with an abnormally high tyrosine hydroxylase/dopa oxidase ratio FEBS J 273 2012 257 270
44. K.H. Kong, M.P. Hong, S.S. Choi, Y.T. Kim, and S.H. Cho Purification of Thermomicrobium roseum tyrosinase Biotechnol Appl Biochem 31 2000 113 118
45. G. Hintermann, M. Zatchej, and R. Hütter Cloning and expression of the genetically unstable tyrosinase structural gene from Streptomyces glaucescens Mol Gen Genet 200 1985 422 432
46. K. Ikeda, T. Masujima, K. Suzuki, and M. Sugiyama Cloning and sequence analysis of the highly expressed melanin-synthesizing gene operon from Streptomyces castaneoglobisporus Appl Microbiol Biotechnol 45 1996 80 85
47. A. Dolashki, A. Gushterova, W. Voelter, and B. Tchorbanov Purification and characterization of tyrosinases from Streptomyces albus Z Naturforsch C 64 2009 724 732
48. V. Shuster, and A. Fishman Isolation, cloning and characterization of a tyrosinase with improved activity in organic solvents from Bacillus megaterium J Mol Microbiol Biotechnol 17 2009 188 200
49. J. Mercado-Blanco, F. Garcia, M. Fernandez-Lopez, and J. Olivares Melanin production by Rhizobium meliloti GR4 is linked to nonsymbiotic plasmid pRmeGR4b: cloning, sequencing, and expression of the tyrosinase gene mepA J Bacteriol 175 1993 5403 5410
50. X. Wan, B. Chai, Y. Liao, Y. Su, T. Ye, and P. Shen Molecular and biochemical characterization of a distinct tyrosinase involved in melanin production from Aeromonas media Appl Microbiol Biotechnol 82 2009 261 269
51. N. Cabrera-Valladares, A. Martinez, S. Pinero, V. Lagunasmunoz, R. Tinoco, and R. Deanda Expression of the melA gene from Rhizobium etli CFN42 in Escherichia coli and characterization of the encoded tyrosinase Enzyme Microb Technol 38 2006 772 779
52. J.D. Bendtsen, H. Nielsen, D. Widdick, T. Palmer, and S. Brunak Prediction of twin-arginine signal peptides BMC Bioinformatics 6 2005 167
53. K. Lerch Primary structure of tyrosinase from Neurospora crassa. II. Complete amino acid sequence and chemical structure of a tripeptide containing an unusual thioether J Biol Chem 257 1982 6414 6419
54. C.D.E. Gielens, N. Geest, X. Xin, B. Devreese, J. Van Beeumen, and G. Preaux Evidence for a cysteine-histidine thioether bridge in functional units of molluscan haemocyanins and location of the disulfide bridges in functional units d and g of the c-haemocyanin of Helix pomatia Eur J Biochem 248 1997 879 888
55. V. Monnet Bacterial oligopeptide-binding proteins Cell Mol Life Sci 60 2003 2100 2114
56. Surwase SN, Patil SA, Apine OA, Jadhav JP. Efficient microbial conversion of l-tyrosine to l-DOPA by Brevundimonas sp. SGJ. Appl Biochem Biotechnol; in press.
57. H.Y. Yang, and C.W. Chen Extracellular and intracellular polyphenol oxidases cause opposite effects on sensitivity of Streptomyces to phenolics: a case of double-edged sword PLoS One 4 2009 e7462
58. D. Lopez-Serrano, F. Solano, and A. Sanchez-Amat Involvement of a novel copper chaperone in tyrosinase activity and melanin synthesis in Marinomonas mediterranea Microbiology 153 2007 2241 2249
59. M. Ito, and K. Oda An organic solvent resistant tyrosinase from Streptomyces sp. REN-21: purification and characterization Biosci Biotech Biochem 64 2000 261 267
60. Goldfeder M, Egozy M, Shuster BYV, Adir N, Fishman A. Changes in tyrosinase specificity by ionic liquids and sodium dodecyl sulphate. Appl Microbiol Biotechnol 2012, http://dx.doi.org/10.1007/s00253-012-4050-z; in press.
61. E. Selinheimo, D. NiEidhin, C. Steffensen, J. Nielsen, A. Lomascolo, and S. Halaouli Comparison of the characteristics of fungal and plant tyrosinases J Biotechnol 130 2007 471 480
62. M. Fairhead, and L. Thöny-Meyer Cross-linking and immobilisation of different proteins with recombinant Verrucomicrobium spinosum tyrosinase J Biotechnol 150 2010 546 551
63. K. Ikeda, T. Masujima, and M. Sugiyama Effects of methionine and Cu2+ on the expression of tyrosinase activity in Streptomyces castaneoglobisporus J Biochem 120 1996 1141 1145
64. A.M. Mayer Polyphenol oxidases in plants and fungi: going places? A review Phytochemistry 67 2006 2318 2331
65. C. Soler-Rivas, A.C. Möller, N. Arpin, J.M. Olivier, and H.J. Wichers Induction of a tyrosinase mRNA in Agaricus bisporus upon treatment with a tolaasin preparation from Pseudomonas tolaasii Physiol Mol Plant Pathol 58 2001 95 99
66. S. Kanda, T. Aimi, S. Masumoto, K. Nakano, Y. Kitamoto, and T. Morinaga Photoregulated tyrosinase gene in Polyporus arcularius Mycoscience 48 2007 34 41
67. G.S. Gukasyan Effect of lignin on growth and tyrosinase activity of fungi from the genus Aspergillus Biochemistry (Moscow) 2012 1999 223 227
68. C.M. Gruhn, and O.K. Miller Jr. Effect of copper on tyrosinase activity and polyamine content of some ectomycorrhizal fungi Mycol Res 95 1991 268 272
69. S. Philipp, T. Held, and H.J. Kutzner Purification and characterization of the tyrosinase of Streptomyces michiganensis DSM 40015 J Basic Microbiol 31 1991 293 300
70. T. Held, and H.J. Kutzner Genetic recombination in Streptomyces michiganensis DSM 40,015 revealed three genes responsible for the formation of melanin J Basic Microbiol 31 1991 127 134
71. N.H. Horowitz, M. Fling, H.M. Feldman, M.L. Pall, and S.C. Froehner Derepression of tyrosinase synthesis in Neurospora by amino acid analogs Dev Biol 21 1970 147 156
72. H.J. Wichers, K. Recourt, M. Hendriks, C.E. Ebbelaar, G. Biancone, and F.A. Hoeberichts Cloning, expression and characterisation of two tyrosinase cDNAs from Agaricus bisporus Appl Microbiol Biotechnol 61 2003 336 341
73. L. Bubacco, E. Vijgenboom, C. Gobin, A.W.J.W. Tepper, J. Salgado, and G.W. Canters Kinetic and paramagnetic NMR investigations of the inhibition of Streptomyces antibioticus tyrosinase J Mol Catal B - Enzym 8 2000 27 35
74. M. Ito, and K. Inouye Catalytic properties of an organic solvent-resistant tyrosinase from Streptomyces sp. REN-21 and its high-level production in E. coli J Biochem 138 2005 355 362
75. G. Wang, A. Aazaz, Z. Peng, and P. Shen Cloning and overexpression of a tyrosinase gene mel from Pseudomonas maltophila FEMS Microbiol Lett 185 2000 23 27
76. V.H. Lagunas-Munoz, N. Cabrera-Valladares, F. Bolivar, G. Gosset, and A. Martinez Optimum melanin production using recombinant Escherichia coli J Appl Microb 101 2006 1002 1008
77. Nishimura I. Acceleration of oxidation reaction of monophenols using tyrosinase. Jpn. Patent. JP 53-121995. 77.03.29; 1978.
78. Fujiwara H. Method for crosslinking polypeptide. Jpn. Patent. JP 2005-287302. 02.04.03; 2005.
79. Fujiwara H. Process for crosslinking polypeptides. Patent. Pub. No. WO/2003/082923. 02.08.09; 2003.
80. J.P. Jadhav, S.S. Phugare, R.S. Dhanve, and S.B. Jadhav Rapid biodegradation and decolorization of Direct Orange 39 (Orange TGLL) by an isolated bacterium Pseudomonas aeruginosa strain BCH Biodegradation 21 2010 453 463
81. Lantto R, Niku-Paavola M, Schonberg C, Buchert J. A tyrosinase enzyme. Intern. Publ. Num. WO 02/14484 A1. 02.02.21; 2002.
82. Thöny-Meyer LC, Fairhead M. Polypeptides having tyrosinase activity and uses thereof. Int. Patent Appl. WO 2011/000121 A1. 10.07.01; 2011.
83. della-Cioppa GR, Garger, SJ, Holtz RB, McCulloch MJ, Sverlow GG. Method for making stable, extracellular tyrosinase and synthesis of polyphenolc polymers therefrom. United States Patent. US 5486351. 96.01.23; 1996.
84. M.S. Paget, G. Hintermann, and C.P. Smith Construction and application of streptomycete promoter probe vectors which employ the Streptomyces glaucescens tyrosinase-encoding gene as reporter Gene 146 1994 105 110
85. Benedict CV. Picciano PT. Method for making dopa-containing bioadhesive proteins from tyrosine-containing proteins. Eur. Patent. EP 0242656 A2. 87.02.04; 1987.
86. D. Ercili Cura, M. Lille, R. Partanen, K. Kruus, J. Buchert, and R. Lantto Effect of Trichoderma reesei tyrosinase on rheology and microstructure of acidified milk gels Int Dairy J 20 2010 830 837
87. G.M.J. Carvalho, T.L.M. Alves, and D.M.G. Freire l-DOPA production by immobilized tyrosinase Appl Biochem Biotechnol 84-86 2000 791 800
88. D. Xu, J. Chen, and Z. Yang Use of cross-linked tyrosinase aggregates as catalyst for synthesis of l-DOPA Biochem Eng J 63 2012 88 94
89. N. Durána, M.A. Rosa, A. D'Annibale, and Gianfreda L Applications of laccases and tyrosinases (phenoloxidases) immobilized on different supports: a review Enzyme Microb Tech 31 2002 907 931
90. G.B. Seetharam, and B.A. Saville Degradation of phenol using tyrosinase immobilized on siliceous supports Water Res. 2012 2003 436 440
91. S. Tuncagil, S.K. Kayahan, G. Bayramoglu, M.Y. Arica, and L. Toppare l-DOPA synthesis using tyrosinase immobilized on magnetic beads J Mol Catal B 58 2009 187 193
92. S. Tembe, M. Karve, S. Inamdar, S. Haram, J. Melo, and S.F. D'Souza Development of electrochemical biosensor based on tyrosinase immobilized in composite biopolymeric film Anal Biochem 349 2006 72 77
93. A. Naidja, P.M. Huang, and J.M. Bollag Activity of tyrosinase immobilized on hydroxyaluminum-montmorillonite complexes J Mol Catal A: Chem 115 1997 305 316
94. P. Pialis, and B.A. Saville Production of l-DOPA from tyrosinase immobilized on nylon 6,6: enzyme stability and scaleup Enzyme Microb Technol 22 1998 261 268
95. G. Seetharam, and B.A. Saville l-DOPA production from tyrosinase immobilized on zeolite Enzyme Microb Technol 31 2002 747 753
96. Peek SM. Method of dyeing animal fibres. United States Patent. US 2539202. 47.12.11; 1951.
97. Warner JC, Stoler EJ. Color composition containing an aromatic compound and tyrosinase. United States Patent. Appl. US 2011/0113571 A1. 10.11.15.
98. T. Yoshio, Y. Yoshiharu, and S. Kuniaki Hair coloring and waiving using oxidases J Soc Cosmet Chem 2012 1991 282
99. J. Abdullah, M. Ahmad, N. Karuppiah, L.Y. Heng, and H. Sidek Immobilization of tyrosinase in chitosan film for an optical detection of phenol Sensors Actuators B: Chem 114 2006 604 609
100. G. Wang, J. Xu, L. Ye, J. Zhu, and H. Chen Highly sensitive sensors based on the immobilization of tyrosinase in chitosan Bioelectrochemistry 57 2002 33 38
101. K. Streffer, E. Vijgenboom, A.W.J.W. Tepper, A. Makower, F.W. Scheller, and G.W. Canters Determination of phenolic compounds using recombinant tyrosinase from Streptomyces antibioticus Anal Chim Acta 427 2001 201 210
102. T. Tatsuma, K. Komori, H. Yeoh, and N. Oyama Disposable test plates with tyrosinase and β-glucosidases for cyanide and cyanogenic glycosides Anal Chim Acta 408 2000 233 240
103. A.M. Girelli, T. Giuliani, E. Mattei, and D. Papaleo Determination of an antioxidant capacity index by immobilized tyrosinase bioreactor J Agric Food Chem 57 2009 5178 5186
104. K.S. Abhijith, P.V. Kumar, M.A. Kumar, and M.S. Thakur Immobilised tyrosinase-based biosensor for the detection of tea polyphenols Anal Bioanal Chem 389 2007 2227 2234
105. Karim F, Fakhruddin ANM. Recent advances in the development of biosensor for phenol: a review. Rev Environ Sci Biotech 2012, http://dx.doi.org/10.1007/ s11157-012-9268-9; in press.
106. L.C. Nolan, and K.E. O'Connor Use of Pseudomonas mendocina, or recombinant Escherichia coli cells expressing toluene-4-monooxygenase, and a cell-free tyrosinase for the synthesis of 4-fluorocatechol from fluorobenzene Biotechnol Lett 7 2007 1045 1050
107. T. Huynh The Parkinson's disease market Nat Rev Drug Discov 10 2011 571 572
108. J.R. Wykes, P. Dunnill, and M.D. Lilly Conversion of tyrosine to l-dihydroxyphenylalanine using immobilized tyrosinase Nat New Biol 230 1971 187
109. R.O. de Faria, V.R. Moure, M.A. Lopes de Almeida Amazonas, N. Krieger, and D.A. Mitchell The biotechnological potential of mushroom tyrosinases Food Technol Biotechnol 45 2007 287 294
110. H.S. Park, J.Y. Lee, and H.S. Kim Production of l-DOPA(3,4- dihydroxyphenyl-l-alanine) from benzene by using a hybrid pathway Biotechnol Bioeng 58 1998 339 343
111. S. Ito, and G. Prota A facile one-step synthesis of cysteinyldopas using mushroom tyrosinase Experientia 33 1977 1118 1119
112. G. Pandey, C. Muralikrishna, and U.T. Bhalerao Mushroom tyrosinase catalysed synthesis of coumestans, bebzofuran derivatives and related heterocyclic compounds Tetrahedron 45 1989 6867 6874
113. Espin de Gea JC, De Tomas Barberan FA, Garcia Viguera MC, Ferreres De Arce F, Soler Rivas C, Wichers H. Enzymatic synthesis of antioxidant hydroxytyrosol. United States Patent. Appl. 20030180833 A1.03.02.11.
114. J.C. Espín, C. Soler-Rivas, E. Cantos, F.A. Tomás- Barberán, and J.H. Wichers Synthesis of the antioxidant hydroxytyrosol using tyrosinase as biocatalyst J Agric Food Chem 49 2001 1187 1193
115. Baranowitz SA. Methods for treating wounds using melanin and related substances. Intern. Publ. Num. WO2003051331A1. 02.10.28; 2003.
116. Berliner DL, Erwin RL, Mcgee DR. Therapeutic uses of melanin. United States Patent. US 5703051. 98.07.07; 1997.
117. E. Greggio, E. Bergantino, D. Carter, R. Ahmad, G.E. Costin, and V.J. Hearing Tyrosinase exacerbates dopamine toxicity but is not genetically associated with Parkinson's disease J Neurochem 93 2005 246 256
118. Lopukhin JM, Zuevsky VV, Rabovsky AB, Andrianov IP. Method for visual indication of cholesterol on skin surface agents used therefor and methods for producing such agents. United States Patent. US 5489510 A. 93.12.09; 1996.
119. S.M. Marino, S. Fogal, M. Bisaglia, S. Moro, G. Scartabelli, and L. De Gioia Investigation of Streptomyces antibioticus tyrosinase reactivity toward chlorophenols Arch Biochem Biophys 505 2011 67 74
120. G. Battaini, E. Monzani, L. Casella, E. Lonardi, A.W. Tepper, and G.W. Canters Tyrosinase-catalyzed oxidation of fluorophenols J Biol Chem 277 2002 44606 44612
121. R.G. Saratale, G.D. Saratale, J.S. Chang, and S.P. Govindwar Bacterial decolorization and degradation of azo dyes: a review J Taiwan Inst Chem E 42 2011 138 157
122. N. Duran, and E. Esposito Potential applications of oxidative enzymes and phenoloxidases-like compounds in wastewater and soil treatment: a review Appl Catalysis B: Environ 28 2000 83 99
123. S. Sani, M.N.M. Muhid, and H. Hamdan Design, synthesis and activity study of tyrosinase encapsulated silica aerogel (TESA) biosensor for phenol removal in aqueous solution J Sol Gel Sci Technol 59 2011 7 18
124. S. Wada, H. Ichikawa, and K. Tatsumi Removal of phenols from wastewater by soluble and immobilized tyrosinase Biotechnol Bioeng 42 1993 854 858
125. K. Yamada, Y. Akiba, T. Shibuya, A. Kashiwada, K. Matsuda, and M. Hirata Water purification through bioconversion of phenol compounds by tyrosinase and chemical adsorption by chitosan beads Biotechnol Prog 21 2008 823 829
126. H.F. Pajot, J.I. Fariña, and L.I.C. de Figueroa Evidence on manganese peroxidase and tyrosinase expression during decolorization of textile industry dyes by Trichosporon akiyoshidainum Int Biodeterior Biodegrad 65 2011 1199 1207
127. R.G. Saratale, G.D. Saratale, J.S. Chang, and S.P. Govindwar Decolorization and biodegradation of textile dye Navy blue HER by Trichosporon beigelii NCIM-3326 J Hazard Mater 166 2009 1421 1428
128. T. Chen, R. Vazquez-Duhalt, C.F. Wu, W.E. Bentley, and G.F. Payne Combinatorial screening for enzyme-mediated coupling. Tyrosinase-catalyzed coupling to create protein-chitosan conjugates Biomacromolecules 2 2001 456 462
129. A. Demolliens, C. Boucher, Y. Durocher, M. Jolicoeur, M.D. Buschmann, and G. De Crescenzo Tyrosinase-catalyzed synthesis of a universal coil-chitosan bioconjugate for protein immobilization Bioconjug Chem 19 2008 1849 1854
130. A. Anghileri, R. Lantto, K. Kruus, C. Arosio, and G. Freddi Tyrosinase-catalyzed grafting of sericin peptides onto chitosan and production of protein-polysaccharide bioconjugates J Biotechnol 127 2007 508 519
131. G.D. Kang, K.H. Lee, C.S. Ki, J.H. Nahm, and Y.H. Park Silk fibroin/chitosan conjugate crosslinked by tyrosinase Macromol Res 12 2004 534 539
132. Barbari TA, Ahmed SR. Affinity membrane for capture of a target biomolecule and formation thereof by site-directed immobilization of a capture molecule. United States Patent. US 2006/0292680 A1. 10.08.10.
133. S.R. Ahmed, A.T. Lutes, and T.A. Barbari Specific capture of target proteins by oriented antibodies bound to tyrosinase-immobilized Protein A on a polyallylamine affinity membrane surface J Mem Sci 2006 311 321
134. S. Jus, V. Kokol, and G.M. Guebitz Tyrosinase-catalysed coating of wool fibres with different protein-based biomaterials J Biomater Sci Polym Ed 20 2 2009 253 269
135. G. Freddi, A. Anghileri, S. Sampaio, J. Buchert, P. Monti, and P. Taddei Tyrosinase-catalyzed modification of Bombyx mori silk fibroin: grafting of chitosan under heterogeneous reaction conditions J Biotech 125 2006 281 294
136. R. Lantto, E. Heine, G. Freddi, A. Lappalainen, A. Miettinen-Oinonen, and M.L. Niku-Paavola Enzymatic modification of wool with tyrosinase and peroxidase J Textile Inst 96 2005 109 116
137. K. Yamada, T. Aoki, N. Ikeda, M. Hirata, Y. Hata, and K. Higashida Application of chitosan solutions gelled by melB tyrosinase to water-resistant adhesives J Appl Polym Sci 107 2008 2723 2731
138. Slaga TJ, Zhao J. Processing method for manufacturing black tea and an improved black tea. United States Patent US 6602527 B1. 00.11.22; 2004.
139. S. Jus, I. Stachel, M. Fairhead, M. Meyer, L. Thöny-Meyer, and G.M. Guebitz Enzymatic cross-linking of gelatine with laccase and tyrosinase Biocatal Biotrans 30 2012 86 95
140. C.I. Onwulata, and P.M. Tomasula Gelling properties of tyrosinase-treated dairy proteins Food Bioprocess Tech 3 2008 554 560
141. S.H. David Casein structure, self-assembly and gelation Curr Opin Colloid Interface Sci 7 2002 456 461
142. E. Selinheimo, P. Lampila, M.L. Mattinen, and J. Buchert Formation of protein-oligosaccharide conjugates by laccase and tyrosinase J Agric Food Chem 56 2008 3118 3128
143. R. Lantto, E. Puolanne, K. Kruus, J. Buchert, and K. Auutio Tyrosinase-aided protein cross-linking: effects on gel formation of chicken breast myofibrils and texture and water-holding of chicken breast meat homogenate gels J Agric Food Chem 55 2007 1248 1255
144. E. Selinheimo, K. Autio, K. Kruus, and J. Buchert Elucidating the mechanism of laccase and tyrosinase in wheat bread making J Agric Food Chem 55 2007 6357 6365
145. S. Takasaki, S. Kawakishi, M. Murata, and S. Homma Polymerisation of gliadin mediated by mushroom tyrosinase Lebensm Wiss Technol 34 2001 507 512
146. Y.W. Luo, W.H. Xie, M. Xu, and F.X. Luo Effects of phytase and polyphenol oxidase treatments on in vitro iron bioavailability in faba bean (Vicia faba L.) CyTA - J Food 2012 1 7
147. Y. Matoba, N. Bando, K. Oda, M. Noda, F. Higashikawa, and T. Kumagai M. Sugiyama A molecular mechanism for copper transportation to tyrosinase that is assisted by a metallochaperone, caddie protein J Biol Chem 286 2011 30219 30231
148. E. Katz, and A. Betancourt Induction of tyrosinase by l-methionine in Streptomyces antibioticus Can J Microbiol 34 1988 1297 1303
149. K. Lerch, and L. Ettinger Purification and characterization of a tyrosinase from Streptomyces glaucescens Eur J Biochem 31 1972 427 437
150. T. Held, and H.J. Kutzner Transcription of the tyrosinase gene in Streptomyces michiganensis DSM 40015 is induced by copper and repressed by ammonium Microbiology 136 1990 2413 2419
151. V.E. Coyne, and L. al-Harthi Induction of melanin biosynthesis in Vibrio cholerae Appl Environ Microbiol 58 1992 2861 2865
152. Uchisawa H, Naraoka T, Takatani Y, Abe K, Yamaguchi SI, Ichida J, Matsue H. Production of water-soluble melanin dyestuff. Jpn. Patent. JP 1996-038187. 94.08.03.
153. Funayama M, Shiyouen S, Yamamoto R. Dyeing of fiber. Jpn. Patent. JP 1997-087977. 97.03.31.
154. Herlihy WC. Skin tanning composition and method. United States Patent. US 4515773. 07.05.1985; 2002.
155. Moon SH, Kim GY. Tyrosinase enzyme electrode and production method thereof. United States Patent US 7935233. 11.05.03; 2009.
156. Arter TC. Multilayer analytical element for salicylate assay. United States Patent. US 5474907. 94.03.25; 1995.
157. Daniel DS, Method and element for assay of catechol and catechol generating substances. Eur. Patent. EP 0464934 A1. 91.06.28; 1992.
158. P. Bouvrette, and J.H.T. Luong A coupled enzymatic assay for salicylate and acetylsalicylate using salicylate hydroxylase and tyrosinase Anal Chim Acta 335 1 1996 69 175
159. C.L. Nolan, and K.E. O'Connor A spectrophotometric method for the quantification of an enzyme activity producing 4-substituted phenols: determination of toluene-4-monooxygenase activity Anal Biochem 344 2005 224 231
160. L. Campanella, E. Gregori, and M. Tomassetti Salicylic acid determination in cow urine and drugs using a bienzymatic sensor J Pharm Bioml Anal 42 2006 94 99
161. A.D. Schweitzer, E. Revskaya, P. Chu, V. Pazo, M. Friedman, and J.D. Nosanchuk Melanin-covered nanoparticles for protection of bone marrow during radiation therapy of cancer Int J Radiat Oncol 78 2010 1494 1502
162. Dantas-Miranda AL. Mosquito deterrent. Patent. WO 2006021834 A1. 04.08.27.
163. Tatsumi K, Takaoichikawa HS. Treatment of chlorophenol-containing water. Jpn. Patent. JP 09239396. 96.03.07; 1997.
164. E. Chiacchierini Bioremediation of food industry effluents: recent applications of free and immobilised polyphenoloxidases Food Sci Technol Int 10 2004 373 382
165. S.C. Atlow, L. Bonadonna-Aparo, and A.M. Klibanov Dephenolization of industrial wastewaters catalyzed by polyphenol oxidase Biotechnol Bioeng 26 1984 599 603
166. Nakamoto S. Method for removing phenols. Jpn. Patent. JP 05-115883. 91.10.25.
167. J.V. Bevilaqua, M.C. Cammarota, D.M.G. Freire, and G.L. Sant'Anna Phenol removal through combined biological and enzymatic treatments Brazil J Chem Eng 19 2002 151 158
168. Asai J. Method for removing COD in drainage water. Jpn. Patent. JP 09-029264. 95.07.17.
169. S.D. Kalme, G.K. Parshetti, S.U. Jadhav, and S.P. Govindwar Biodegradation of benzidine based dye Direct Blue-6 by Pseudomonas desmolyticum NCIM 2112 Bioresour Technol 98 2007 1405 1410
170. S. Kalme, G. Ghodake, and S. Govindwar Red HE7B degradation using desulfonation by Pseudomonas desmolyticum NCIM 2112 Int Biodeterior Biodegrad 60 2007 327 333
171. C.C. Oturkar, H.N. Nemade, P.M. Mulik, M.S. Patole, R.R. Hawaldar, and K.R. Gawai Mechanistic investigation of decolorization and degradation of Reactive Red 120 by Bacillus lentus BI377 Bioresour Technol 102 2011 758 764
172. F. Gandía-Herrero, J. Escribano, and F. García-Carmona Characterization of the activity of tyrosinase on betanidin J Agric Food Chem 55 2007 1546 1551
173. Della-Cioppa GR, Garger SJ, Holtz RB, McCulloch MJ, Sverlow GG. Method for making stable, extracellular tyrosinase and synthesis of polyphenolic polymers therefrom. United States Patent. US 5466592A. 93.12.14; 1985.
174. Miyakoshi T. Coating composition. Jpn. Patent. JP 05-117591 A. 91.12.29; 1993.
175. Nishimatsu M. Film forming method. Jpn Patent. JP 63-294967 A. 87.05.26.
176. Ellis J, Cornell DL. A method for treating proteinaceous fibres. Eur. Patent EP 1311 719 B1. 01.08.15; 2003.
177. Ellis J, Cornell DL. Treating proteinaceous materials - precision processes textiles limited. Int. Patent. WO/2003/069051. 03.02.10.
178. Zhao J, Slaga TJ, Fields C. High yield process for producing theaflavins and products of such process. United States Patent. US 20040137129 A1. 03.11.18.
179. Y.Y. Tu, X.Q. Xu, H.L. Xia, and N. Watanabe Optimization of theaflavin biosynthesis from tea polyphenols using an immobilized enzyme system and response surface methodology Biotech Lett 27 2005 269 274
180. Autio K, Lille M, Myllarinen P. Milk product and method for its preparation. WIPO Patent Appl. WO/2007/141385 A1. 07.06.05.
181. Uchiyama S. Method and reagent for counting microorganism. Jpn. Patent. JP 06-113892 A. 92.10.01; 1994.
182. V. Bernan, D. Filpula, W. Herber, M. Bibb, and E. Katz The nucleotide sequence of the tyrosinase gene from Streptomyces antibioticus and characterization of the gene product Gene 37 1985 101 110