title: Dopaquinone hydroxylation through topaquinone cofactor in copper amine oxidases: a simplified chemical model.
abstract: A simple model, 4-tert-butyl-1,2-benzoquinone, was chosen to study the hydroxylation step of the tyrosine-derived Dopaquinone residue at the active site of copper amine oxidases in the self-catalytic generation of the Topaquinone cofactor. This hydroxylation step was studied both in the presence and absence of free copper(II), and was found to be dependent on pH value but not on the presence of metal ions. It is therefore proposed that, hydroxide ion and not water should be the true reactive species in this key biosynthetic step of the Topaquinone cofactor, and that the active site Cu2+ is implied, at this point of cofactor biosynthesis, in the quinonisation of Topa rather than in the hydroxylation of Dopaquinone.
authors.affiliation: Dipartimento di Medicina Sperimentale e Scienze Biochimiche, Università di Roma Tor Vergata, Italy.
authors.forename: A C
authors.initials: AC
authors.lastname: Rinaldi
authors.forename: A
authors.initials: A
authors.lastname: Rescigno
authors.forename: F
authors.initials: F
authors.lastname: Sollai
authors.forename: G
authors.initials: G
authors.lastname: Soddu
authors.forename: N
authors.initials: N
authors.lastname: Curreli
authors.forename: A
authors.initials: A
authors.lastname: Rinaldi
authors.forename: A
authors.initials: A
authors.lastname: Finazzi-Agrò
authors.forename: E
authors.initials: E
authors.lastname: Sanjust
mesh_terms: D006631:Amine Oxidase (Copper-Containing) / Q000378:metabolism*; D016227:Benzoquinones / Q000378:metabolism*; D004295:Dihydroxyphenylalanine / Q000031:analogs & derivatives* / Q000378:metabolism; D006900:Hydroxylation; D008956:Models, Chemical
chemical_list: D016227:Benzoquinones; D004295:Dihydroxyphenylalanine; C067626:6-hydroxydopa quinone; C035157:dopaquinone; D006631:Amine Oxidase (Copper-Containing)