Synthesis and characterization of models for the 2,4, 5-trihydroxyphenylalanine (TOPA)-derived cofactor of mammalian copper amine oxidases, and initial amine reactivity studies

Three models having more consistent structural resemblance to the quinone form (TPQ) of a protein found in mammalian copper amine oxidase active sites are synthesized. These models differ in the nature of alkyl substituent. These quinone forms deaminate benzylamine in aqueous CH3CN, both catalytically and stoichiometrically. The pH-dependent benzenetriol to hydroxyquinone autooxidation and amine reaction with benzenetriol forms are examined to analyze aerobic autorecycling deamination.