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

Authors
Rinaldi, AC Ponticelli, G Oliva, S Di Giulio, A Sanjust, E
Citation
Ac. Rinaldi et al., 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, BIOORG MED, 10(9), 2000, pp. 989-992
Citations number
27
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
10
Issue
9
Year of publication
2000
Pages
989 - 992
Database
ISI
SICI code
0960-894X(20000501)10:9<989:COTO4T>2.0.ZU;2-B
Abstract
Topaquinone (TPQ) is a cofactor present at the active site of copper amine oxidases, derived from a Tyr residue inserted in the polypeptide chain thro ugh a copper-dependent but otherwise largely unknown mechanism. A simple mo del 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-hydr oxyquinonic structure in the presence of Cu(II)-imidazole mononuclear compl exes. (C) 2000 Elsevier Science Ltd. All rights reserved.