Garcia-Ramos, Marina, Cuetos, Anibal, Kroutil, Wolfgang et al. (2 more authors) (2022) The Reactivity of α-Fluoroketones with PLP Dependent Enzymes: Transaminases as Hydrodefluorinases. ChemCatChem. pp. 3967-3972. ISSN 1867-3899
Abstract
A chemical method for the treatment of harmful halogenated compounds that has recently become of interest is the reductive dehalogenation of carbon–halogen bonds. In the case of a fluorine atom, this process is called hydrodefluorination. While many transition metal-based approaches now exist to reductively defluorinate aromatic fluoroarenes, the cleavage of C–F bonds in aliphatic compounds is not so well-developed. Here we propose a biocatalytic approach exploiting a promiscuous activity exhibited by transaminases (TAs). Hence, a series of α-fluoroketones have been defluorinated with excellent conversions using Chromobacterium violaceum and Arthrobacter sp. TAs under mild conditions and in aqueous medium, using a stoichiometric amount of an amine (e.g. 2-propylamine) as reagent and formally releasing its oxidized form (e.g. acetone), with ammonia and hydrogen fluoride as by-products. It is also demonstrated that this process can be performed in a regio- or stereoselective fashion.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2021 The Authors. ChemCatChem published by Wiley-VCH GmbH. |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 10 Aug 2021 10:40 |
Last Modified: | 18 Mar 2025 00:09 |
Published Version: | https://doi.org/10.1002/cctc.202100901 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1002/cctc.202100901 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:176909 |