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Non-symmetrically substituted phenoxazinones from laccase-mediated oxidative cross-coupling of aminophenols: an experimental and theoretical insight.

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Bruyneel, Frédéric [UCL] Dive, Georges [ULg] Marchand-Brynaert, Jacqueline [UCL]

Oxidative cross-coupling reactions of substituted o-aminophenols were catalyzed by a commercial laccase to produce non-symmetrically substituted phenoxazinones for the first time. Identification by 1H-, 13C- and 31P-NMR, and by HPLC-PDA and HPLC-MS/MS of exclusively two kinds of substituted phenoxazinones out of four potential heterocyclic frameworks was confirmed by a DFT study. The redox-properties of the substrates, their relative rates of conversion and the rigid docking of selected substrates led to a revisited mechanistic pathway for phenoxazinones biosynthesis. Our suggestions concern both the first formal two-electron oxidation by laccase and the first intermolecular 1,4-conjugated addition which secures the observed regioselectivity.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2012
Language Anglais
Journal information "Organic & Biomolecular Chemistry" - Vol. 10, no. 9, p. 1834-1846 (2012)
Peer reviewed yes
Publisher Royal Society of Chemistry
issn 1477-0520
Publication status Publié
Affiliations UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
ULg - Centre Ingénirie des protéines
Links
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Bibliographic reference Bruyneel, Frédéric ; Dive, Georges ; Marchand-Brynaert, Jacqueline. Non-symmetrically substituted phenoxazinones from laccase-mediated oxidative cross-coupling of aminophenols: an experimental and theoretical insight.. In: Organic & Biomolecular Chemistry, Vol. 10, no. 9, p. 1834-1846 (2012)
Permanent URL http://hdl.handle.net/2078.1/107832