A hydroxyquinone with amine oxidase activity: preparation and properties.
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.
Sanjust
E
E
Istituto di Chimica Biologica, Università degli Studi, Cagliari, Italy.
Rinaldi
A C
AC
Rescigno
A
A
Porcu
M C
MC
Alberti
G
G
Rinaldi
A
A
Finazzi-Agrò
A
A
D006631:Amine Oxidase (Copper-Containing); D000588:Amines / Q000737:chemistry*; D016227:Benzoquinones / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D010084:Oxidation-Reduction; D000587:Oxidoreductases Acting on CH-NH Group Donors / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship
D000588:Amines; D016227:Benzoquinones; D011809:Quinones; C087484:2-hydroxy-5-methylquinone; D006631:Amine Oxidase (Copper-Containing); D000587:Oxidoreductases Acting on CH-NH Group Donors