A study on the electrochemical synthesis of L-DOPA using oxidoreductase enzymes: optimization of an electrochemical process

J Microbiol Biotechnol. 2012 Oct;22(10):1446-51. doi: 10.4014/jmb.1206.06043.

Abstract

Levodopa or L-3,4-dihydroxyphenylalanine (L-DOPA) is the precursor of the neurotransmitter dopamine. L-DOPA is a famous treatment for Parkinson's disease symptoms. In this study, electroenzymatic synthesis of L-DOPA was performed in a three-electrode cell, comprising a Ag/AgCl reference electrode, a platinum wire auxiliary electrode, and a glassy carbon working electrode. L-DOPA had an oxidation peak at 376 mV and a reduction peak at -550 mV. The optimum conditions of pH, temperature, and amount of free tyrosinase enzyme were pH 7, 30 degrees C, and 250 IU, respectively. The kinetic constant of the free tyrosinase enzyme was found for both cresolase and catacholase activity to be 0.25 and 0.4 mM, respectively. A cyclic voltammogram was used to investigate the electron transfer rate constant. The mean heterogeneous electron transfer rate (ke) was 5.8 × 10(-4) cm/s. The results suggest that the electroenzymatic method could be an alternative way to produce L-DOPA without the use of a reducing agent such as ascorbic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoquinones / chemistry
  • Carbon / chemistry
  • Dihydroxyphenylalanine / analogs & derivatives
  • Dihydroxyphenylalanine / chemistry
  • Electrochemical Techniques / methods*
  • Electrodes
  • Electron Transport
  • Electrons
  • Enzyme Activation
  • Enzyme Assays / methods*
  • Hydrogen-Ion Concentration
  • Levodopa / chemical synthesis*
  • Levodopa / chemistry
  • Monophenol Monooxygenase / chemistry
  • Oxidation-Reduction
  • Platinum / chemistry
  • Silver / chemistry
  • Silver Compounds / chemistry

Substances

  • Benzoquinones
  • Silver Compounds
  • Silver
  • Levodopa
  • Platinum
  • Dihydroxyphenylalanine
  • Carbon
  • dopaquinone
  • Monophenol Monooxygenase
  • silver chloride