TY - JOUR
T1 - Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles
AU - Branco, Paula Cristina de Sério
AU - Ferreira, Luísa Maria da Silva Pinto
AU - Pereira, Maria Alice Santos
PY - 2012/1/1
Y1 - 2012/1/1
N2 - 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.
AB - 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.
U2 - 10.1016/j.bioorg.2012.05.002
DO - 10.1016/j.bioorg.2012.05.002
M3 - Article
C2 - 22784829
SN - 0045-2068
VL - 44
SP - 19
EP - 24
JO - Bioorganic Chemistry
JF - Bioorganic Chemistry
IS - NA
ER -