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

被引：14

作者：

Bruyneel, Frederic ^{[1
]}

Dive, Georges ^{[2
]}

Marchand-Brynaert, Jacqueline ^{[1
]}

机构：

[1] Catholic Univ Louvain, Organ & Med Chem CHOM, Inst Condensed Matter & Nanosci IMCN, B-1348 Louvain, Belgium

[2] Univ Liege, Ctr Ingn Proteines, B-4000 Liege, Belgium

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 09期

关键词：

TRAMETES-VERSICOLOR LACCASE; 3-HYDROXYANTHRANILIC ACID; CRYSTAL-STRUCTURE; ELECTRON-TRANSFER; STERIC ISSUES; BASIS-SET; SYNTHASE; MECHANISM; LIGNIN; REDOX;

D O I：

10.1039/c1ob05795b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

引用

页码：1834 / 1846

页数：13

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