Abstract
H2O2-driven enzymes are of great interest for industrial
biotransformations. Herein, we show for the first time that oxalate
oxidase (OXO) is an efficient in situ source of H2O2 for one of these
biocatalysts, which is known as unspecific peroxygenase (UPO). OXO
is reasonably robust, produces only CO2 as a by-product and uses
oxalate as a cheap sacrificial electron donor. UPO has significant
potential as an industrial catalyst for selective C-H
oxyfunctionalisations, as we confirm herein by testing a diverse drug
panel using miniaturised high-throughput assays and mass
spectrometry. 33 out of 64 drugs were converted in 5 μL-scale
reactions by the UPO with OXO (conversion >70% for 11 drugs).
Furthermore, oxidation of the drug tolmetin was achieved on a 50 mg
scale (TONUPO 25,664) with 84% yield, which was further improved
via enzyme immobilization. This one-pot approach ensures adequate
H2O2 levels, enabling rapid access to industrially relevant molecules
that are difficult to obtain by other routes.
biotransformations. Herein, we show for the first time that oxalate
oxidase (OXO) is an efficient in situ source of H2O2 for one of these
biocatalysts, which is known as unspecific peroxygenase (UPO). OXO
is reasonably robust, produces only CO2 as a by-product and uses
oxalate as a cheap sacrificial electron donor. UPO has significant
potential as an industrial catalyst for selective C-H
oxyfunctionalisations, as we confirm herein by testing a diverse drug
panel using miniaturised high-throughput assays and mass
spectrometry. 33 out of 64 drugs were converted in 5 μL-scale
reactions by the UPO with OXO (conversion >70% for 11 drugs).
Furthermore, oxidation of the drug tolmetin was achieved on a 50 mg
scale (TONUPO 25,664) with 84% yield, which was further improved
via enzyme immobilization. This one-pot approach ensures adequate
H2O2 levels, enabling rapid access to industrially relevant molecules
that are difficult to obtain by other routes.
Original language | English |
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Article number | e202207831 |
Number of pages | 7 |
Journal | Angewandte Chemie International Edition |
Early online date | 2 Aug 2022 |
DOIs | |
Publication status | E-pub ahead of print - 2 Aug 2022 |