doi: 10.1016/j.bioorg.2012.05.002.
Epub 2012 Jun 19.
Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles
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- PMID: 22784829
- DOI: 10.1016/j.bioorg.2012.05.002
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Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles
Bioorg Chem.
2012 Oct.
Abstract
The enzymatic (tyrosinase) and chemical (NaIO(4), Ag(2)O 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.
Copyright © 2012 Elsevier Inc. All rights reserved.
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