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Sequential Enzymatic Oxidation of Aminoarenes to Nitroarenes via Hydroxylamines^†

Robert Winkler

Leibniz Institute for Natural Products Research and Infection Biology, HKI, Beutenbergstrasse 11a, 07745 Jena, Germany, Fax: (+49) 3641-656-705

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Christian Hertweck,

Christian Hertweck

[email protected]

Leibniz Institute for Natural Products Research and Infection Biology, HKI, Beutenbergstrasse 11a, 07745 Jena, Germany, Fax: (+49) 3641-656-705

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Robert Winkler,

Robert Winkler

Leibniz Institute for Natural Products Research and Infection Biology, HKI, Beutenbergstrasse 11a, 07745 Jena, Germany, Fax: (+49) 3641-656-705

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Christian Hertweck,

Christian Hertweck

[email protected]

Leibniz Institute for Natural Products Research and Infection Biology, HKI, Beutenbergstrasse 11a, 07745 Jena, Germany, Fax: (+49) 3641-656-705

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First published: 17 June 2005

https://doi.org/10.1002/anie.200500365

Citations: 71

^†

We thank the Deutsche Forschungsgemeinschaft for financial support in the priority program SPP1152 “Evolution of Metabolic Diversity” (HE 3469/2) and A. Perner for MS measurements.

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Graphical Abstract

The at-line detection of an amino group oxidation catalyzed by the N-oxygenase AurF provides the first direct evidence for a stepwise enzymatic oxidation of aromatic amines to nitro groups via a hydroxylamine intermediate (see scheme). The sequential nature of this reaction is further supported by biotransformation of the intermediate and the identification of a p-aminobenzoate-derived azoxy side product.

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Volume44, Issue26

June 27, 2005

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Sequential Enzymatic Oxidation of Aminoarenes to Nitroarenes via Hydroxylamines^†

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Sequential Enzymatic Oxidation of Aminoarenes to Nitroarenes via Hydroxylamines^†