Oxidation of amides by laccase-generated aminoxyl radicals
作者： Alessandra Coniglio , Carlo Galli , Patrizia Gentili , Raffaella Vadalà
DOI: 10.1016/J.MOLCATB.2007.09.022
关键词: Reactivity (chemistry) 、 Chemistry 、 Trametes villosa 、 Organic chemistry 、 Medicinal chemistry 、 Radical 、 Enzyme catalysis 、 Laccase
摘要: Abstract The enzyme laccase from the fungus Trametes villosa catalyses oxidation of two hydroxylamines ( NO H), i.e., HPI (N-hydroxy-phthalimide) and HBT (1-hydroxy-benzotriazole), into their corresponding aminoxyl radicals ) PINO BTNO. ensuing a few amides lactames by BTNO has been investigated in buffered water solution (pH 5) at room temperature. results this chemo-enzymatic approach have compared with literature method that generates radical HPI/Co(II)/O2 chemical system, uses it for similar amides. merits comparatively assessed method, mechanism investigated. A Hammett treatment relative reactivity X-substituted-N-acetylbenzylamides competition experiments supports rate-determining H-abstraction route. With substrates, stereoelectronic effects uncovered, rationalisation contribution to route is offered, supported semiempirical calculations.
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