TAILIEUCHUNG - Báo cáo Y học: Agmatine oxidation by copper amine oxidase Biosynthesis and biochemical characterization of N-amidino-2-hydroxypyrrolidine

The product of agmatine oxidation catalyzed by Pisum sativum L. copper amine oxidase has been identified by means of one- and two-dimensional 1H-NMR spectroscopy to be N-amidino-2-hydroxypyrrolidine. This compound inhibits competitively rat nitric oxide synthase type I and type II (NOS-I and NOS-II, respectively) and bovine trypsin (trypsin) activity, values of Ki being ( ± ) · 10)5 M (at pH and °C), ( ± ) · 10)5 M (at pH and °C), and ( ± ) · 10)5 M (at pH and °C), respectively. . | Eur. J. Biochem. 269 884-892 2002 FEBS 2002 Agmatine oxidation by copper amine oxidase Biosynthesis and biochemical characterization of Mamidino-2-hydroxypyrrolidine Paolo Ascenzi1 I Mauro Fasano Maria Marino1 Giorgio Venturini1 and Rodolfo Federico1 1 Department of Biology University Roma Tre Rome Italy department of Structural and Functional Biology University of Insubria Varese Italy The product of agmatine oxidation catalyzed by Pisum sativum L. copper amine oxidase has been identified by means of one- and two-dimensional 1H-NMR spectroscopy to be N-amidino-2-hydroxypyrrolidine. This compound inhibits competitively rat nitric oxide synthase type I and type II NOS-I and NOS-II respectively and bovine trypsin trypsin activity values of Ki being X 10-5M at pH and C X 10-5 M at pH and C and X 10-5 M atpH C respectively. Remarkably the affinity of N-amidino-2-hydroxypyrrolidine for NOS-I NOS-II and trypsin is significantly higher than that observed for agmatine and clonidine binding. Furthermore N-amidino-2-hydroxy-pyrrolidine and agmatine are more efficient than clonidine in displacing 3H clonidine X 10-8 m from specific binding sites in heart rat membranes values of IC50 being X 10-9 M and X 10-8 M respectively at pH and C . Keywords copper amine oxidase agmatine N-amidino-2-hydroxypyrrolidine enzyme inhibition type 1 imidazoline receptor binding. Copper amine oxidase has been identified in bacteria yeasts fungi plants and animals. This enzyme is a homodimer of 70- to 90-kDa subunits each containing a single copper ion and a covalently bound cofactor formed by the post-translational modification of the catalytic tyrosyl residue to 2 4 5-trihydroxyphenylalanine quinone TPQ 1-4 . Copper amine oxidase catalyzes the oxidative deamination of biogenic amines including mono di and polyamines neurotransmitters such as catecholamines histamine and xenobiotic amines with substrate preferences

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