ArticleNature communications2024
Reaction engineering blocks ether cleavage for synthesizing chiral cyclic hemiacetals catalyzed by unspecific peroxygenase.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 18 citations in OpenAlex.
- Exploiting the Intrinsic Peroxidase Activity of Unspecific Peroxygenase for the Oxidative Cyclization of Ortho-Substituted Phenols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Enhanced secretion of an Agrocybe aegerita peroxygenase variant in K. phaffii using the native signal peptide.AMB Express · 2026Article
- Computational rational design of unspecific peroxygenase for C-H oxidation.Science advances · 2026Article
- Unspecific Peroxygenases for the Enzymatic Removal of Alkyl Protecting Groups in Organic Synthesis.ACS catalysis · 2025Article
Corrections and comments
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Authors and funding
8 authors at 3 institutions in 2 countries.
Funding
Abstract
Hemiacetal compounds are valuable building blocks in synthetic chemistry, but their enzymatic synthesis is limited and often hindered by the instability of hemiacetals in aqueous environments. Here, we show that this challenge can be addressed through reaction engineering by using immobilized peroxygenase from Agrocybe aegerita (AaeUPO) under neat reaction conditions, which allows for the selective C-H bond oxyfunctionalization of environmentally significant cyclic ethers to cyclic hemiacetals. A wide range of chiral cyclic hemiacetal products are prepared in >99% enantiomeric excess and 95170 turnover numbers of AaeUPO. Furthermore, by changing the reaction medium from pure organic solvent to alkaline aqueous conditions, cyclic hemiacetals are in situ transformed into lactones. Lactams are obtained under the applied conditions, albeit with low enzyme activity. These findings showcase the synthetic potential of AaeUPO and offer a practical enzymatic approach to produce chiral cyclic hemiacetals through C-H oxyfunctionalization under mild conditions.
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Registered trials
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