Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles

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Abstract

The enzymatic (tyrosinase) and chemical (NaIO(4), Ag(2)O 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.
Original languageUnknown
Pages (from-to)19-24
JournalBioorganic Chemistry
Volume44
Issue numberNA
DOIs
Publication statusPublished - 1 Jan 2012

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