Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles

Citation:
Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles, Siopa, Filipa, Pereira Alice S., Ferreira Luisa M., Matilde Marques M., and Branco Paula S. , BIOORGANIC CHEMISTRY, Oct, Volume {44}, 525 B ST, STE 1900, SAN DIEGO, CA 92101-4495 USA, p.{19-24}, (2012) copy at https://sites.fct.unl.pt/molecular-biophysics/publications/synthesis-catecholamine-conjugates-nitrogen-centered-bionucleophil

Abstract:

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.

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