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Article Dans Une Revue Journal of Organic Chemistry Année : 2000

Oxidative Deamination of Benzylamine by Electrogenerated Quinonoid Systems as Mimics of Amine Oxidoreductases Cofactors

Résumé

The reactions of a new type of quinonoid systems with benzylamine have been investigated in methanol in order to mimic the reactions occurring in the course of the enzymatic oxidation of amines by quinone cofactors. Under strictly anaerobic conditions, unstable quinonoid species 1ox-4ox have been selectively electrogenerated using anodic controlled potential electrolysis. Thus, we have demonstrated that 3,4-quinone 1ox is incapable of deaminating benzylamine, while 3,4-iminoquinone species 3ox and 4ox act as efficient catalysts for the autorecycling oxidation of benzylamine : the reaction efficiency reached 64 turnovers. Additional mechanistic investigations reveal that the oxidation of benzylamine by our quinonoid model cofactors proceeds unambiguously via a transamination mechanism as suggested for many enzymatic systems.
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hal-02385121 , version 1 (24-05-2022)

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Martine Largeron, Maurice-Bernard Fleury. Oxidative Deamination of Benzylamine by Electrogenerated Quinonoid Systems as Mimics of Amine Oxidoreductases Cofactors. Journal of Organic Chemistry, 2000, 65 (26), pp.8874-8881. ⟨10.1021/jo000478l⟩. ⟨hal-02385121⟩

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