| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1356327 | Bioorganic Chemistry | 2012 | 6 Pages |
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.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► 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.
