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 Cu 2+ 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.
A hydroxyquinone with amine oxidase activity: preparation and properties
SANJUST, ENRICO;RINALDI, ANDREA;RESCIGNO, ANTONIO;
1995-01-01
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 Cu 2+ 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.
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