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Your search keyword '"Bruyneel, Frédéric"' showing total 2 results
Start Over Author "Bruyneel, Frédéric" Publisher royal society of chemistry
2 results on '"Bruyneel, Frédéric"'

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

Author

UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity, ULg - Centre Ingénirie des protéines, Bruyneel, Frédéric, Dive, Georges, Marchand-Brynaert, Jacqueline, UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity, ULg - Centre Ingénirie des protéines, Bruyneel, Frédéric, Dive, Georges, and Marchand-Brynaert, Jacqueline

Abstract

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.

Published
2012

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

Author

Bruyneel F, Dive G, and Marchand-Brynaert J

Subjects
Aminophenols metabolism, Biological Products chemistry, Models, Molecular, Molecular Structure, Oxidation-Reduction, Stereoisomerism, Substrate Specificity, Aminophenols chemistry, Laccase metabolism, Oxazines chemical synthesis, Trametes enzymology
Abstract

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 (1)H-, (13)C- and (31)P-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.

Published
2012
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