A hydroxyquinone with amine oxidase activity: preparation and properties

Biochem Biophys Res Commun. 1995 Mar 17;208(2):825-34. doi: 10.1006/bbrc.1995.1411.

Abstract

The preparation and some properties of a hydroxyquinone showing an amine oxidase-like activity are described. The compound, 2-hydroxy-5-methyl-1,4-benzoquinone, oxidizes a wide range of primary amines, both benzylic and non-benzylic, at the expenses of molecular oxygen in the presence of Cu2+ ions, and reacts with hydrazine derivatives leading to stable, inactive adducts. This behaviour is similar to that of 2,4,5-trihydroxyphenylalanine quinone-containing amine oxidases and therefore the present compound could be a useful model to understand the reaction mechanism of those enzymes.

MeSH terms

  • Amine Oxidase (Copper-Containing)*
  • Amines / chemistry*
  • Benzoquinones / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Oxidation-Reduction
  • Oxidoreductases Acting on CH-NH Group Donors / chemistry*
  • Quinones / chemistry*
  • Spectrum Analysis
  • Structure-Activity Relationship

Substances

  • Amines
  • Benzoquinones
  • Quinones
  • 2-hydroxy-5-methylquinone
  • Amine Oxidase (Copper-Containing)
  • Oxidoreductases Acting on CH-NH Group Donors