Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles.
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.
Chemistry Department, REQUIMTE, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.
Filipa
F
Siopa
Alice S
AS
Pereira
Luísa M
LM
Ferreira
M
M
Matilde Marques
Paula S
PS
Branco
D000363:Agaricales / Q000201:enzymology*; D002395:Catecholamines / Q000737:chemistry* / Q000378:metabolism*; D014442:Monophenol Monooxygenase / Q000378:metabolism*; D009584:Nitrogen / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction; D011809:Quinones / Q000737:chemistry / Q000378:metabolism
D002395:Catecholamines; D011809:Quinones; D014442:Monophenol Monooxygenase; D009584:Nitrogen