Isolation, cloning and characterization of a tyrosinase with improved activity in organic solvents from bacillus megaterium

Journal of Molecular Microbiology and Biotechnology

Volumn 17, Issue 4, 2009, Pages 188-200

  Shuster, Vered ^a   Fishman, Ayelet ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

Bacillus megaterium; Diphenolase activity; L Tyrosine; Monophenolase activity; Organic solvents; Tyrosinase

Indexed keywords

2 PROPANOL; ALCOHOL; COPPER SULFATE; DIMETHYL SULFOXIDE; LEVODOPA; METHANOL; MONOPHENOL MONOOXYGENASE; ORGANIC SOLVENT; RIBOSOME DNA; TYROSINE;

ARTICLE; BACILLUS MEGATERIUM; DENATURATION; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME ISOLATION; ESCHERICHIA COLI; GENE AMPLIFICATION; MISCIBILITY; NONHUMAN;

AMINO ACID SEQUENCE; BACILLUS MEGATERIUM; BACTERIAL PROTEINS; CLONING, MOLECULAR; DNA, BACTERIAL; DNA, RIBOSOMAL; ENZYME ACTIVATORS; ENZYME STABILITY; ESCHERICHIA COLI; GENE EXPRESSION; HYDROGEN-ION CONCENTRATION; KINETICS; LEVODOPA; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; MONOPHENOL MONOOXYGENASE; ORGANIC CHEMICALS; RNA, RIBOSOMAL, 16S; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS, DNA; SOIL MICROBIOLOGY; SOLVENTS; TEMPERATURE; TYROSINE;

BACILLUS MEGATERIUM; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 70350339292     PISSN: 14641801     EISSN: None     Source Type: Journal    
DOI: 10.1159/000233506     Document Type: Article

References (61)

1. Abhijith KS, Kumar PV, Kumar MA, Thakur MS: Immobilised tyrosinase-based biosensor for the detection of tea polyphenols. Anal Bioanal Chem 2007; 389: 2227-2234.
2. Ates S, Cortenlioglu E, Bayraktar E, Mehmetoglu U: Production of L -DOPA using Cu-alginate gel immobilized tyrosinase in a batch and packed bed reactor. Enzyme Microb Technol 2007; 40: 683-687.
3. Berglund P: Controlling lipase enantioselectivity for organic synthesis. Biomol Eng 2001; 18: 13-22.
4. Burton SG: Oxidizing enzymes as biocatalysts. Trends Biotechnol 2003a;21: 543-549.
5. Burton SG: Laccases and phenol oxidases in organic synthesis -a review. Curr Org Chem 2003b;7: 1317-1331.
6. Cabrera-Valladares N, Martinez A, Pinero S, Lagunas-Munoz HV, Tinoco R, Anda R, Vazquez-Duhalt R, Bolivar F, Gosset G: Expression of the melA gene from Rhizobium etli CFN42 in Escherichia coli and characterization of the encoded tyrosinase. Enzyme Microb Technol 2006; 38: 772-779.
7. Carrea G, Ottolina G, Riva S: Role of solvents in the control of enzyme selectivity in organic media. Trends Biotechnol 1995; 13: 63-70.
8. Casella L, Gullotti M, Poli S, Bonfa M, Ferrari RP, Marchesini A: Spectroscopic and binding studies on the stereoselective interaction of tyrosine with horseradish peroxidase and lactoperoxidase. Biochem J 1991; 279(part 1):245-250.
9. Chen T, Embree HD, Wu LQ, Payne GF: In vitro protein-polysaccharide conjugation: tyrosinase-catalyzed conjugation of gelatin and chitosan. Biopolymers 2002; 64: 292-302.
10. Claus H, Decker H: Bacterial tyrosinases. Syst Appl Microbiol 2006; 29: 3-14.
11. Dalfard AB, Kajeh K, Soudi MR, Naderi-Manesh H, Ranjbar B, Sajedi RH: Isolation and biochemical characterization of laccase and tyrosinase activities in a novel melanogenic soil bacterium. Enzyme Microb Technol 2006; 39: 1409-1416.
12. Decker H, Tuczek F: Tyrosinase/catecholoxidase activity of hemocyanins: structural basis and molecular mechanism. Trends Biochem Sci 2000; 25: 392-397.
13. Duran N, Esposito E: Potential applications of oxidative enzymes and phenoloxidase-like compounds in wastewater and soil treatment: a review. Appl Catal B 2000; 28: 83-99.
14. Duran N, Rosa MA, D'Annibale A, Gianfreda L: Applications of laccases and tyrosinases (phenoloxidases) immobilized on different supports: a review. Enzyme Microb Technol 2002; 31: 907.
15. Espin JC, Wichers HJ: Activation of a latent mushroom ( Agaricus bisporus ) tyrosinase isoform by sodium dodecyl sulfate (SDS): kinetic properties of the SDS-activated isoform. J Agric Food Chem 1999; 47: 3518-3525.
16. Espin JC, Garcia-Ruiz PA, Tudela J, Garcia-Canovas F: Study of stereospecificity in mushroom tyrosinase. Biochem J 1998a;331: 547-551.
17. Espin JC, Garcia-Ruiz PA, Tudela J, Garcia-Canovas F: Study of stereospecificity in pear and strawberry polyphenol oxidases. J Agric Food Chem 1998b;46: 2469-2473.
18. Espin JC, Soler-Rivas C, Cantos E, Tomas-Barberan FA, Wichers HJ: Synthesis of the antioxidant hydroxytyrosol using tyrosinase as biocatalyst. J Agric Food Chem 2001; 49: 1187-1193.
19. Gandia-Herrero F, Jimenez-Atienzar M, Cabanes J, Garcia-Carmona F, Escribano J: Differential activation of a latent polyphenol oxidase mediated by sodium dodecyl sulfate. J Agric Food Chem 2005; 53: 6825-6830.
20. Garcia-Molina F, Munoz JL, Garcia-Ruýz PA, Rodriguez-Lopez JN, Garcia-Canovas F, Tudela J: A further step in the kinetic characterisation of the tyrosinase enzymatic system. J Math Chem 2006; 41: 393-406.
21. Garcia-Molina F, Munoz JL, Varon R, Rodriguez-Lopez JN, Garcia-Canovas F, Tudela J: A review on spectrophotometric methods for measuring the monophenolase and diphenolase activities of tyrosinase. J Agric Food Chem 2007; 55: 9739-9749. (Pubitemid 350305154)
22. Girelli AM, Mattei E, Messina A: Phenols removal by immobilized tyrosinase reactor in on-line high performance liquid chromatography. Anal Chim Acta 2006; 580: 271-277.
23. Gupta MN, Roy I: Enzymes in organic media: forms, functions and applications. Eur J Biochem 2004; 271: 2575-2583.
24. Halaouli S, Asther M, Kruus K, Guo L, Hamdi M, Sigoillot JC, Asther M, Lomascolo A: Characterization of a new tyrosinase from Pycnoporus species with high potential for food technological applications. J Appl Microbiol 2005; 98: 332-343.
25. Halaouli S, Asther M, Sigoillot JC, Hamdi M, Lomascolo A: Fungal tyrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications. J Appl Microbiol 2006; 100: 219-232.
26. Hernàndez-Romero D, Sanchez-Amat A, Solano F: A tyrosinase with an abnormally high tyrosine hydroxylase/dopa oxidase ratio. FEBS J 2006; 273: 257-270.
27. Intra A, Nicotra S, Riva S, Danieli B: Significant and unexpected solvent influence on the selectivity of laccase-catalyzed coupling of tetrahydro-2-naphthol derivatives. Adv Synth Catal 2005; 347: 973-977.
28. Ito M, Oda K: An organic solvent resistant tyrosinase from Streptomyces sp. REN-21: purification and characterization. Biosci Biotechnol Biochem 2000; 64: 261-267.
29. Katz E, Thompson CJ, Hopwood DA: Cloning and expression of the tyrosinase gene from Streptomyces antibioticus in Streptomyces lividans . J Gen Microbiol 1983; 129: 2703-2714.
30. Kawamura-Konishi Y, Tsuji M, Hatana S, Asanuma M, Kakuta D, Kawano T, Mukouyama EB, Goto H, Suzuki H: Purification, characterization, and molecular cloning of tyrosinase from Pholiota nameko . Biosci Biotechnol Biochem 2007; 71: 1752-1760.
31. Kawashiro K, Sugahara H, Sugiyama S, Hayashi H: Effect of organic solvents on enantioselectivity of protease catalysis. Biotechnol Bioeng 1997; 53: 26-31.
32. Kermasha S, Tse M: Biocatalysis of tyrosinase in chloroform medium, using selected phenolic substrates. J Chem Technol Biotechnol 2000; 75: 475-483.
33. Kermasha S, Bao H, Bisakowski B: Biocatalysis of tyrosinase using catechin as substrate in selected organic solvent media. J Mol Catal B Enzym 2001; 11: 929-938.
34. Kilbanov AM: Improving enzymes by using them in organic solvents. Nature 2001; 409: 241-246.
35. Kohashi PY, Kumagai T, Matoba Y, Yamamoto A, Maruyama M, Sugiyama M: An efficient method for the overexpression and purification of active tyrosinase from Streptomyces castaneoglobisporus . Protein Expr Purif 2004; 34: 202-210.
36. Kong KH, Hong MP, Choi SS, Kim YT, Cho SH: Purification and characterization of a highly stable tyrosinase from Thermomicrobium roseum . Biotechnol Appl Biochem 2000; 31: 113-118.
37. Lerch K, Ettinger L: Purification and characterization of a tyrosinase from Streptomyces glaucescens . Eur J Biochem 1972; 31: 427-437.
38. Liu N, Zhang T, Wang YJ, Huang YP, Ou JH, Shen P: A heat inducible tyrosinase with distinct properties from Bacillus thuringiensis . Lett Appl Microbiol 2004; 39: 407-412.
39. Lopez-Serrano D, Sanchez-Amat A, Solano F: Cloning and molecular characterization of a SDS-activated tyrosinase from Marinomonas mediterranea. Pigment Cell Res 2002; 15: 104-111.
40. Martinez MV, Whitaker JR: The biochemistry and control of enzymatic browning. Trends Food Sci Technol 1995; 6: 195-202.
41. Matoba Y, Kumagai T, Yamamoto A, Yoshitsu H, Sugiyama M: Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis. J Biol Chem 2006; 281: 8981-8990.
42. McMahon AM, Doyle EM, Brooks S, O'Connor KE: Biochemical characterisation of the coexisting tyrosinase and laccase in the soil bacterium Pseudomonas putida F6. Enzyme Microb Technol 2007; 40: 1435-1441.
43. Ogel ZB, Yuzugullu Y, Mete S, Bakir U, Kaptan Y, Sutay D, Demir AS: Production, properties and application to biocatalysis of a novel extracellular alkaline phenol oxidase from the thermophilic fungus Scytalidium thermophilum . Appl Microbiol Biotechnol 2006; 71: 853-862.
44. Olivares C, Garcia-Borron JC, Solano F: Identification of active site residues involved in metal cofactor binding and stereospecific substrate recognition in mammalian tyrosinase: implications to the catalytic cycle. Biochemistry 2002; 41: 679-686.
45. Rasko DA, Ravel J, Okstad OA, Helgason E, Cer RZ, Jiang L, Shores KA, Fouts DE, Tourasse NJ, Angiuoli SV, Kolonay J, Nelson WC, Kolsto AB, Fraser CM, Read TD: The genome sequence of Bacillus cereus ATCC 10987 reveals metabolic adaptations and a large plasmid related to Bacillus anthracis pXO1. Nucleic Acids Res 2004; 32: 977-988.
46. Ruan L, He W, He J, Sun M, Yu Z: Cloning and expression of mel gene from Bacillus thuringiensis in Escherichia coli . Antonie Van Leeuwenhoek 2005; 87: 283-288.
47. Sambrook J, Russell DW: Molecular Cloning: A Laboratory Manual, ed 3. New York, Cold Spring Harbor Laboratory Press, 2001.
48. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B: Industrial biocatalysis today and tomorrow. Nature 2001; 409: 258-268.
49. Selinheimo E, Gasparetti C, Mattinen ML, Steffensen CL, Buchert J, Kruus K: Comparison of substrate specificity of tyrosinases from Trichoderma reesei and Agaricus bisporus . Enzyme Microb Technol 2009; 44: 1-10.
50. Selinheimo E, Saloheimo M, Ahola E, Westerholm-Parvinen A, Kalkkinen N, Buchert J, Kruus K: Production and characterization of a secreted, C-terminally processed tyrosinase from the filamentous fungus Trichoderma reesei . FEBS J 2006; 273: 4322-4335.
51. Selinheimo E, NiEidhin D, Steffensen C, Nielsen J, Lomascolo A, Halaouli S, Record E, O'Beirne D, Buchert J, Kruus K: Comparison of the characteristics of fungal and plant tyrosinases. J Biotechnol 2007; 130: 471-480.
52. Seo SY, Sharma VK, Sharma N: Mushroom tyrosinase: recent prospects. J Agric Food Chem 2003; 51: 2837-2853.
53. Sun J, Wang W, Hundertmark C, Zeng AP, Jahn D, Deckwer WD: A protein database constructed from low-coverage genomic sequence of Bacillus megaterium and its use for accelerated proteomic analysis. J Biotechnol 2006; 124: 486-495.
54. Tanimoto de Albuquerque YD, Ferreira LF: Amperometric biosensing of carbamate and organophosphate pesticides utilizing screenprinted tyrosinase-modified electrodes. Anal Chim Acta 2007; 596: 210-221.
55. Tse M, Kermasha S, Ismail A: Biocatalysis by tyrosinase in organic solvent media: a model system using catechin and vanillin as substrates. J Mol Catal B Enzym 1997; 2: 199-213.
56. Valero E, Varon R, Garcia-Carmona F: Inhibition of grape polyphenol oxidase by several natural aliphatic alcohols. J Agric Food Chem 1990; 38: 1097-1100.
57. Wescott CR, Noritomi H, Klibanov AM: Rational Control of Enzymatic Enantioselectivity through solvation thermodynamics. J Am Chem Soc 1996; 118: 10365-10370.
58. Westerholm-Parvinen A, Selinheimo E, Boer H, Kalkkinen N, Mattinen M, Saloheimo M: Expression of the Trichoderma reesei tyrosinase 2 in Pichia pastoris : isotopic labeling and physicochemical characterization. Protein Expr Purif 2007; 55: 147-158.
59. Wittenberg C, Triplett EL: A detergent-activated tyrosinase from Xenopus laevis . II. Detergent activation and binding. J Biol Chem 1985; 260: 12542-12546. (Pubitemid 16233456)
60. Yang Z, Russell AJ: Fundamentals of non-aqueous enzymology; in Koskinen A, Klibanov A (eds): Enzymatic Reactions in Organic Media. London, Blackie Academic & Professional, 1996, pp 43-65.
61. Yu B, Chang TMS: In vitro and in vivo enzyme studies of polyhemoglobin-tyrosinase. Biotechnol Bioeng 2004; 86: 835-841.