Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles

Filipa Siopa; Alice S Pereira; Luísa M Ferreira; M Matilde Marques; Paula S Branco

doi:10.1016/j.bioorg.2012.05.002

Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles

Bioorg Chem. 2012 Oct:44:19-24. doi: 10.1016/j.bioorg.2012.05.002. Epub 2012 Jun 19.

Authors

Filipa Siopa¹, Alice S Pereira, Luísa M Ferreira, M Matilde Marques, Paula S Branco

Affiliation

¹ Chemistry Department, REQUIMTE, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.

PMID: 22784829
DOI: 10.1016/j.bioorg.2012.05.002

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Agaricales / enzymology*
Catecholamines / chemistry*
Catecholamines / metabolism*
Monophenol Monooxygenase / metabolism*
Nitrogen / chemistry
Nitrogen / metabolism*
Oxidation-Reduction
Quinones / chemistry
Quinones / metabolism

Substances

Catecholamines
Quinones
Monophenol Monooxygenase
Nitrogen