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Abstract
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. (Figure presented.).
Original language | English |
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Pages (from-to) | 37-42 |
Number of pages | 6 |
Journal | Advanced Synthesis and Catalysis |
Volume | 365 |
Issue number | 1 |
DOIs | |
Publication status | Published - 10 Jan 2023 |
Keywords
- aldoxime dehydratase (Oxd)
- carboxylic acid reductase (CAR)
- chemoenzymatic synthesis
- cyanide-free nitrile synthesis
- nitriles
- oxidoreductases
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Fields of Expertise
- Human- & Biotechnology
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Dive into the research topics of 'Organic Acid to Nitrile: a chemoenzymatic three-step route'. Together they form a unique fingerprint.Projects
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FWF - Nitriles - A new chemoenzymatic route from carboxylic acids to nitriles
1/03/20 → 1/08/24
Project: Research project