Copper-promoted overall transformation of 4-tert-butylphenol to its para-hydroxyquinonic derivative, 2-hydroxy-5-tert-butyl-1,4-benzoquinone. Biomimetic studies on the generation of topaquinone in copper amine oxidases.
Topaquinone (TPQ) is a cofactor present at the active site of copper amine oxidases, derived from a Tyr residue inserted in the polypeptide chain through a copper-dependent but otherwise largely unknown mechanism. A simple model system was developed that permits to obtain the overall transformation of 4-tert-butylphenol, chosen as a model for Tyr, into a TPQ-like, para-hydroxyquinonic structure in the presence of Cu(II)-imidazole mononuclear complexes.
Rinaldi
A C
AC
Cattedra di Chimica Biologica, Dipartimento di Scienze Mediche Internistiche, Università di Cagliari, Monserrato, Italy. rinaldi@vaxcal.unica.it
Ponticelli
G
G
Oliva
S
S
Di Giulio
A
A
Sanjust
E
E
D006631:Amine Oxidase (Copper-Containing) / Q000378:metabolism*; D016227:Benzoquinones / Q000138:chemical synthesis*; D003300:Copper / Q000737:chemistry*; D004295:Dihydroxyphenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D006900:Hydroxylation; D008239:Lysine / Q000031:analogs & derivatives / Q000737:chemistry; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry
C414804:2-hydroxy-5-tert-butyl-1,4-benzoquinone; D016227:Benzoquinones; D010636:Phenols; D011809:Quinones; C100796:lysine tyrosylquinone; D004295:Dihydroxyphenylalanine; C067626:6-hydroxydopa quinone; D003300:Copper; D006631:Amine Oxidase (Copper-Containing); D008239:Lysine; C006862:butylphen