L-DOPA Synthesis Using Tyrosinase-immobilized on Electrode Surfaces

Siti Fauziyah Rahman; Siramulu Gobikhrisnan; Misri Gozan; Gwi Taek Jong; Don-Hee Park

Korean Chemical Engineering Research, Vol.54, No.6, 817-821, December, 2016

DOI10.9713/kcer.2016.54.6.817 Export Citation

L-DOPA Synthesis Using Tyrosinase-immobilized on Electrode Surfaces

Siti Fauziyah Rahman, Siramulu Gobikhrisnan¹, Misri Gozan², Gwi Taek Jong³, and Don-Hee Park^{4, †}

Interdisciplinary Program of Graduate School for Bioenergy and Biomaterials, Chonnam National University, 77, Yongbong-ro, Buk-gu, Gwangju, 61186, Korea
¹Department of Bioscience and Technology, Karunya University, Coimbatore, 641114, India
²Bioprocess Engineering Research Group, Chemical Engineering Department, Faculty of Engineering, Universitas Indonesia, Kampus UI Depok, 16424, Indonesia
³Department of Biotechnology and Bioengineering, Pukyong National University, 45, Yongso-ro, Nam-gu, Busan, 48513, Korea
⁴Department of Biotechnology and Bioengineering, Chonnam National University, 77, Yongbong-ro, Buk-gu, Gwangju, 61186, Korea

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Levodopa or L-3,4-dihydroxyphenylalanine (L-DOPA) is the direct precursor of the neurotransmitter dopamine. L-DOPA is a well-known neuroprotective agent for the treatment of Parkinson’s disease symptoms. L-DOPA was synthesized using the enzyme, tyrosinase, as a biocatalyst for the conversion of L-tyrosine to L-DOPA and an electrochemical method for reducing L-DOPAquinone, the product resulting from enzymatic synthesis, to L-DOPA. In this study, three electrode systems were used: A glassy carbon electrode (GCE) as working electrode, a platinum, and a Ag/AgCl electrode as auxiliary and reference electrodes, respectively. GCE has been modified using electropolymerization of pyrrole to facilitate the electron transfer process and immobilize tyrosinase. Optimum conditions for the electropolymerization modified electrode were a temperature of 30 °C and a pH of 7 producing L-DOPA concentration 0.315 mM. After 40 days, the relative activity of an enzyme for electropolymerization remained 38.6%, respectively.

Keywords:L-DOPA synthesis;Tyrosinase-immobilized;Electrode surface;Parkinson’s disease

[References]

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[2] Knowles WS, Sabacky MJ, Vineyad, L-DOPA process and intermediates, United States Patent. US4005127 (1977).

[3] Koyanagi T, Katayama T, Suzuki H, Nakazawa H, Yokozeki K, Kumagai H, J. Biotechnol., 115, 303 (2005)

[4] Sayyed IA, Sudalai A, Tetrahedron: Asymmetry, 15, 3111 (2004)

[5] Park HS, Lee JY, Kim HS, Biotechnol. Bioeng., 58(2-3), 339 (1998)

[6] Kyanagi T, Katayama T, Suzuki H, Nakazawa H, Yokozeki K, Kumagai H, J. Biotechnol., 115, 303 (2005)

[7] Huang SY, Shen YW, Chan HS, Enzyme Microb. Technol., 30(6), 779 (2002)

[8] Krishnaveni R, Rathod V, Nagur R, Kulkarni P, Desai P, Int. J. Curr. Microbiol. App. Sci., 4(10), 350 (2015)

[9] Wei T, Cheng BY, Liu JZ, Sci. Rep., 6, 30080 (2016)

[10] Min K, Park K, Park DH, Yoo YJ, Appl. Microbiol. Biotechnol., 99(2), 575 (2015)

[11] Zaborsky, Oskar, Immoblized Enzymes, CRC Press, Ohio (1974).

[12] Guisan JM, Immobilization of Enzyme and Cells, Human Press, Totowa (2006).

[13] Rahman SF, Min K, Park SH, Park JH, Yoo JC, Park DH, Korean J. Chem. Eng., 10.1007/s11814-016-0207-2 (2016)

[14] Yildiz HB, Caliskan S, Kamaci M, Caliskan A, Int. J. Biol. Macromol., 56, 34 (2013)

[15] Min K, Park DH, Yoo YJ, J. Biotechnol., 146, 40 (2010)

[16] Rahman SF, Gobikishnan S, Indrawan N, Park SH, Park JH, Min K, Yoo YJ, Park DH, J. Microbiol. Biotechnol., 22, 1446 (2012)

[17] Venugopal N, Kim WS, Korean J. Chem. Eng., 32(9), 1918 (2015)

[18] Sadki S, Schottland P, Brodie N, Sabouraud G, Chem. Soc. Rev., 29, 283 (2000)

[19] Liu X, Zhang Z, Cheng G, Dong S, Electroanalysis, 15, 2 (2003)

[20] Ramanavicius A, Ramanaviciene A, Malinauskas A, Electrochim. Acta, 27, 6025 (2006)

[21] Erdogan H, Tuncagil S, Toppare L, J. Macromol. Sci. A, 47, 209 (2010)

[22] Kumar A, Gross RA, Biomacromolecules, 1(1), 133 (2000)

[23] Cao X, Zhang R, Tan WM, Wei C, Wang J, Liu ZM, Chen KQ, Quyang PK, Korean J. Chem. Eng., 33(5), 1653 (2016)