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- W2031142152 abstract "Copper amine oxidases are a family of enzymes with quinone cofactors that oxidize primary amines to aldehydes. The native mechanism proceeds via an iminoquinone intermediate that promotes high selectivity for reactions with primary amines, thereby constraining the scope of potential biomimetic synthetic applications. Here we report a novel bioinspired quinone catalyst system consisting of 1,10-phenanthroline-5,6-dione/ZnI2 that bypasses these constraints via an abiological pathway involving a hemiaminal intermediate. Efficient aerobic dehydrogenation of non-native secondary amine substrates, including pharmaceutically relevant nitrogen heterocycles, is demonstrated. The ZnI2 cocatalyst activates the quinone toward amine oxidation and provides a source of iodide, which plays an important redox-mediator role to promote aerobic catalytic turnover. These findings provide a valuable foundation for broader development of aerobic oxidation reactions employing quinone-based catalysts." @default.
- W2031142152 created "2016-06-24" @default.
- W2031142152 creator A5037348586 @default.
- W2031142152 creator A5074617275 @default.
- W2031142152 date "2013-12-18" @default.
- W2031142152 modified "2023-09-29" @default.
- W2031142152 title "Bioinspired Aerobic Oxidation of Secondary Amines and Nitrogen Heterocycles with a Bifunctional Quinone Catalyst" @default.
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- W2031142152 doi "https://doi.org/10.1021/ja411692v" @default.
- W2031142152 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3985088" @default.
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- W2031142152 hasPublicationYear "2013" @default.
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