Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles

Siopa, F., AS Pereira, LM Ferreira, M. M. Marques, and P. S. Branco. "Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles." Bioorganic Chemistry. 44 (2012): 19-24.


The enzymatic (tyrosinase) and chemical (NaIO4, Ag2O or Fremys's salt) oxidation of biologically relevant catecholamines, such as dopamine (DA), N-acetyldopamine (NADA) and the Ecstasy metabolites (alpha-MeDA and N-Me-alpha-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. (C) 2012 Elsevier Inc. All rights reserved.


Times Cited: 0 Siopa, Filipa Pereira, Alice S. Ferreira, Luisa M. Matilde Marques, M. Branco, Paula S.

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