Winkler, M., Horvat, M., Schiefer, A., Weilch, V., Rudroff, F., Pátek, M., & Martínková, L. (2023). Organic Acid to Nitrile: A Chemoenzymatic Three‐Step Route. Advanced Synthesis & Catalysis, 365(1). https://doi.org/10.1002/adsc.202201053
Various widely applied compounds contain cyano-groups, and this functional group serves as a chemical handle for a whole range of different reactions. We report a cyanide free chemoenzymatic cascade for nitrile synthesis. The reaction pathway starts with a reduction of carboxylic acid to aldehyde by carboxylate reductase enzymes (CARs) applied as living cell biocatalysts. The second – chemical – step includes in situ oxime formation with hydroxylamine. The final direct step from oxime to nitrile is catalyzed by aldoxime dehydratases (Oxds). With compatible combinations of a CAR and an Oxd, applied in one-pot two-step reactions, several aliphatic and aryl-aliphatic target nitriles were obtained in more than 80% conversion. Phenylacetonitrile, for example, was prepared in 78% isolated yield. This chemoenzymatic route does not require cyanide salts, toxic metals, or undesired oxidants in contrast to entirely chemical procedures.
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Research Areas:
Sustainable Production and Technologies: 80% Efficient Utilisation of Material Resources: 20%
