Grogan, Gideon James orcid.org/0000-0003-1383-7056, Pogranyi, Balazs, Mielke, Tamara et al. (3 more authors) (2022) Preparative-Scale Biocatalytic Oxygenation of N-Heterocycles with a Lyophilized Peroxygenase Catalyst. Angewandte Chemie International Edition. e202214759. ISSN 1433-7851
Abstract
A lyophilized preparation of an unspecific peroxygenase variant from Agrocybe aegerita (rAaeUPO-PaDa-I-H) is a highly effective catalyst for the oxygenation of a diverse range of Nheterocyclic compounds. Scalable biocatalytic oxygenations (27 preparative examples, ≈100 mgs scale) have been developed across a wide range of substrates, including alkyl pyridines, bicyclic Nheterocycles and indoles. H2O2 is the only stoichiometric oxidant needed, without auxiliary electron transport proteins, which is key to the practicality of the method. Reaction outcomes can be altered depending on whether hydrogen peroxide was delivered by syringe pump or through in situ generation using an alcohol oxidase from Pichia pastoris (PpAOX) and methanol as a co-substrate. Good synthetic yields (up to 84%), regioselectivity and enantioselectivity (up to 99% ee) were observed in some cases, highlighting the promise of UPOs as practical, versatile and scalable oxygenation biocatalysts.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2022 The Authors. |
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: | 05 Dec 2022 13:30 |
Last Modified: | 04 Jan 2025 00:21 |
Published Version: | https://doi.org/10.1002/anie.202214759 |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1002/anie.202214759 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:194097 |
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Description: Angew Chem Int Ed - 2022 - Pogr nyi - Preparative‐Scale Biocatalytic Oxygenation of N‐Heterocycles with a Lyophilized
Licence: CC-BY 2.5