Singlet oxygen generation during the oxidation of L-tyrosine and L-dopa with mushroom tyrosinase

Biochem Biophys Res Commun. 2016 Mar 18;471(4):450-3. doi: 10.1016/j.bbrc.2016.02.056. Epub 2016 Feb 17.

Abstract

The generation of singlet oxygen during the oxidation of tyrosine and L-dopa using mushroom tyrosinase in a phosphate buffer (pH 7.4), the model of melanin synthesis in melanocytes, was examined. The reaction was performed in the presence of 2,2,6,6-tetramethyl-4-piperidone (4-oxo-TEMP), an acceptor of singlet oxygen and the electron spin resonance (ESR) of the spin adduct, 4-oxo-2,2,6,6-tetramethyl-1-piperidinyloxy (4-oxo-TEMPO), was measured. An increase in the ESR signal attributable to 4-oxo-TEMPO was observed during the oxidation of tyrosine and L-dopa with tyrosinase, indicating the generation of singlet oxygen. The results suggest that (1)O2 generation via tyrosinase-catalyzed melanin synthesis occurs in melanocyte.

Keywords: ESR; Oxidative stress; Singlet oxygen; Tyrosinase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / enzymology
  • Electron Spin Resonance Spectroscopy
  • Indolequinones / metabolism
  • Levodopa / metabolism*
  • Melanins / biosynthesis
  • Melanins / metabolism
  • Monophenol Monooxygenase / metabolism*
  • Oxidation-Reduction
  • Piperidines / analysis
  • Piperidines / metabolism
  • Singlet Oxygen / metabolism*
  • Superoxides / metabolism
  • Tyrosine / metabolism*

Substances

  • 4-oxo-2,2,6,6-tetramethyl-1-piperidinyloxyl
  • Indolequinones
  • Melanins
  • Piperidines
  • Superoxides
  • Singlet Oxygen
  • dopachrome
  • Tyrosine
  • Levodopa
  • Monophenol Monooxygenase