Enantioselective biocatalytic formal α-amination of hexanoic acid to L-norleucine

Alexander Dennig; Somayyeh Gandomkar; Emmanuel Cigan; Tamara C. Reiter; Thomas Haas; Mélanie Hall; Kurt Faber

doi:10.1039/C8OB02212G

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Enantioselective biocatalytic formal α-amination of hexanoic acid to l-norleucine†

Alexander Dennig,

^a Somayyeh Gandomkar,

^a Emmanuel Cigan,^a Tamara C. Reiter,^a Thomas Haas,^b Mélanie Hall

*^a and Kurt Faber

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria
E-mail: melanie.hall@uni-graz.at, kurt.faber@uni-graz.at

^b Creavis, Evonik Industries, Bau 1420, Paul Baumann Strasse 1, 45772 Marl, Germany

Abstract

A three-step one-pot biocatalytic cascade was designed for the enantioselective formal α-amination of hexanoic acid to L-norleucine. Regioselective hydroxylation by P450_CLA peroxygenase to 2-hydroxyhexanoic acid was followed by oxidation to the ketoacid by two stereocomplementary dehydrogenases. Combination with final stereoselective reductive amination by amino acid dehydrogenase furnished L-norleucine in >97% ee.

This article is part of the themed collection: Catalysis & biocatalysis in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB02212G
Article type: Communication
Submitted: 07 Sep 2018
Accepted: 05 Oct 2018
First published: 05 Oct 2018

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Org. Biomol. Chem., 2018,16, 8030-8033

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Enantioselective biocatalytic formal α-amination of hexanoic acid to L-norleucine

A. Dennig, S. Gandomkar, E. Cigan, T. C. Reiter, T. Haas, M. Hall and K. Faber, Org. Biomol. Chem., 2018, 16, 8030 DOI: 10.1039/C8OB02212G

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Organic & Biomolecular Chemistry

Enantioselective biocatalytic formal α-amination of hexanoic acid to l-norleucine†

Abstract

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Enantioselective biocatalytic formal α-amination of hexanoic acid to L-norleucine

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