Selective Epoxidation of Fatty Acids and Fatty Acid Methyl Esters by Fungal Peroxygenases

• Published in: ChemCatChem Vol. 10; no. 18; pp. 3964 - 3968
• Main Authors: Aranda, Carmen, Olmedo, Andrés, Kiebist, Jan, Scheibner, Katrin, del Río, José C., Martínez, Angel T., Gutiérrez, Ana
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 20.09.2018
• Subjects: Chaetomium globosum; Conversion; Epoxidation; Esters; fatty acid methyl esters; Fatty acids; fungal peroxygenases; Fungi; oxidoreductases; Selectivity; Substrates
• ISSN: 1867-3880; 1867-3899
• DOI: 10.1002/cctc.201800849

Recently discovered fungal unspecific peroxygenases from Marasmius rotula and Chaetomium globosum catalyze the epoxidation of unsaturated fatty acids (FA) and FA methyl esters (FAME), unlike the well‐known peroxygenases from Agrocybe aegerita and Coprinopsis cinerea. Reactions of a series of unsaturated FA and FAME with cis‐configuration revealed high (up to 100 %) substrate conversion and selectivity towards epoxidation, although some significant differences were observed between enzymes and substrates with the best results being obtained with the C. globosum enzyme. This and the M. rotula peroxygenase appear as promising biocatalysts for the environmentally‐friendly production of reactive FA epoxides given their self‐sufficient monooxygenase activity and the high conversion rate and epoxidation selectivity. DIRECT enzymatic epoxidation: Recently discovered fungal unspecific peroxygenases from Marasmius rotula and Chaetomium globosum catalyze the epoxidation of unsaturated fatty acids (FA) and FA methyl esters (FAME), unlike the well‐known peroxygenases from Agrocybe aegerita and Coprinopsis cinerea. Reactions of a series of unsaturated FA and FAME revealed high substrate conversion (with up to 8000 total turnover number in oleic acid reactions) and selectivity towards epoxidation (often >90 %), the best results being obtained with the C. globosum enzyme.