Organic Acid to Nitrile: A Chemoenzymatic Three-Step Route

0568108 - MBÚ 2024 RIV DE eng J - Journal Article
Winkler, M. - Horvat, M. - Schiefer, A. - Weilch, V. - Rudroff, F. - Pátek, Miroslav - Martínková, Ludmila
Organic Acid to Nitrile: A Chemoenzymatic Three-Step Route.
Advanced Synthesis & Catalysis. Roč. 365, č. 1 (2023), s. 37-42. ISSN 1615-4150. E-ISSN 1615-4169
R&D Projects: GA ČR(CZ) GF20-23532L
Institutional support: RVO:61388971
Keywords : chemoenzymatic synthesis * carboxylic acid reductase (CAR) * aldoxime dehydratase (Oxd) * cyanide-free nitrile synthesis * nitriles * oxidoreductases
OECD category: Biochemistry and molecular biology
Impact factor: 5.4, year: 2022
Method of publishing: Open access
https://onlinelibrary.wiley.com/doi/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.
Permanent Link: https://hdl.handle.net/11104/0342525