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Article

Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases

1
Instituto de Recursos Naturales y Agrobiología de Sevilla, Consejo Superior de Investigaciones Científicas (CSIC), 41012 Seville, Spain
2
Johnson Matthey, Cambridge Science Park U260, Cambridge CB4 0FP, UK
3
Institute of Biotechnology, Brandenburg University of Technology Cottbus-Senftenberg, 01968 Senftenberg, Germany
4
Unit of Bio- and Environmental Sciences, International Institute Zittau, TU Dresden, 02763 Zittau, Germany
5
Centro de Investigaciones Biológicas “Margarita Salas”, Consejo Superior de Investigaciones Científicas (CSIC), 28040 Madrid, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: Stanley Omaye
Antioxidants 2022, 11(3), 522; https://doi.org/10.3390/antiox11030522
Received: 10 February 2022 / Revised: 1 March 2022 / Accepted: 7 March 2022 / Published: 8 March 2022
(This article belongs to the Special Issue Dream Peroxygenases)
Terminal alkenes are among the most attractive starting materials for the synthesis of epoxides, which are essential and versatile intermediate building blocks for the pharmaceutical, flavoring, and polymer industries. Previous research on alkene epoxidation has focused on the use of several oxidizing agents and/or different enzymes, including cytochrome P450 monooxygenases, as well as microbial whole-cell catalysts that have several drawbacks. Alternatively, we explored the ability of unspecific peroxygenases (UPOs) to selectively epoxidize terminal alkenes. UPOs are attractive biocatalysts because they are robust extracellular enzymes and only require H2O2 as cosubstrate. Here, we show how several UPOs, such as those from Cyclocybe (Agrocybe) aegerita (AaeUPO), Marasmius rotula (MroUPO), Coprinopsis cinerea (rCciUPO), Humicola insolens (rHinUPO), and Daldinia caldariorum (rDcaUPO), are able to catalyze the epoxidation of long-chain terminal alkenes (from C12:1 to C20:1) after an initial optimization of several reaction parameters (cosolvent, cosubstrate, and pH). In addition to terminal epoxides, alkenols and other hydroxylated derivatives of the alkenes were formed. Although all UPOs were able to convert and epoxidize the alkenes, notable differences were observed between them, with rCciUPO being responsible for the highest substrate turnover and MroUPO being the most selective with respect to terminal epoxidation. The potential of peroxygenases for epoxidizing long-chain terminal alkenes represents an interesting and green alternative to the existing synthesis technologies. View Full-Text
Keywords: peroxygenases; oxyfunctionalization; epoxidation; terminal alkenes; epoxides peroxygenases; oxyfunctionalization; epoxidation; terminal alkenes; epoxides
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MDPI and ACS Style

Babot, E.D.; Aranda, C.; Kiebist, J.; Scheibner, K.; Ullrich, R.; Hofrichter, M.; Martínez, A.T.; Gutiérrez, A. Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases. Antioxidants 2022, 11, 522. https://doi.org/10.3390/antiox11030522

AMA Style

Babot ED, Aranda C, Kiebist J, Scheibner K, Ullrich R, Hofrichter M, Martínez AT, Gutiérrez A. Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases. Antioxidants. 2022; 11(3):522. https://doi.org/10.3390/antiox11030522

Chicago/Turabian Style

Babot, Esteban D., Carmen Aranda, Jan Kiebist, Katrin Scheibner, René Ullrich, Martin Hofrichter, Angel T. Martínez, and Ana Gutiérrez. 2022. "Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases" Antioxidants 11, no. 3: 522. https://doi.org/10.3390/antiox11030522

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