Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles

The enzymatic (tyrosinase) and chemical (NaIO4, Ag2O or Frémys’s salt) oxidation of biologically relevant catecholamines, such as dopamine (DA), N-acetyldopamine (NADA) and the Ecstasy metabolites (α-MeDA and N-Me-α-MeDA) generates the corresponding o-quinone which can be trapped with nitrogen bionucleophiles such as N-acetyl-histidine and imidazole in a regioselective reaction that takes place predominantly at the 6-position of the catecholamine.

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► First enzymatic and chemical synthesis of nitrogen–catecholamine adducts.
► Full spectroscopic analysis of nitrogen–catecholamine adducts.
► Regioselective reaction at the 6-position of the catecholamines.
► Allows the availability of synthetic standards.