Chemoenzymatic one-pot reaction from carboxylic acid to nitrile via oxime

Melissa Horvat; Victoria Weilch; Robert Rädisch; Sebastian Hecko; Astrid Schiefer; Florian Rudroff; Birgit Wilding; Norbert Klempier; Miroslav Pátek; Ludmila Martínková; Margit Winkler

doi:10.1039/D1CY01694F

Chemoenzymatic one-pot reaction from carboxylic acid to nitrile via oxime†

Melissa Horvat,^a Victoria Weilch,^a Robert Rädisch,

^bc Sebastian Hecko,^d Astrid Schiefer,^d Florian Rudroff,

^d Birgit Wilding,

^ef Norbert Klempier,^f Miroslav Pátek,^b Ludmila Martínková*^b and Margit Winkler

*^ae

Author affiliations

* Corresponding authors

^a Institute of Molecular Biotechnology, Graz University of Technology, Petersgasse 14, A-8010 Graz, Austria
E-mail: margit.winkler@tugraz.at

^b Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-142 20 Prague, Czech Republic
E-mail: martinko@biomed.cas.cz

^c Department of Genetics and Microbiology, Faculty of Science, Charles University, Viničná 5, CZ-12844 Prague 2, Czech Republic

^d Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/OC-163, A-1060 Vienna, Austria

^e Acib GmbH, Krenngasse 37, A-8010 Graz, Austria

^f Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria

Abstract

We report a new chemoenzymatic cascade starting with aldehyde synthesis by carboxylic acid reductase (CAR) followed by chemical in situ oxime formation. The final step to the nitrile is catalyzed by aldoxime dehydratase (Oxd). Full conversions of phenylacetic acid and hexanoic acid were achieved in a two-phase mode.

Catalysis Science & Technology

Chemoenzymatic one-pot reaction from carboxylic acid to nitrile via oxime†

Abstract

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Chemoenzymatic one-pot reaction from carboxylic acid to nitrile via oxime

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