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Selective Oxygenation of Ionones and Damascones by Fungal Peroxygenases

AuthorsBabot, Esteban Daniel ; Aranda, Carmen; Río Andrade, José Carlos del ; Ullrich, René; Kiebist, Jan; Scheibner, Katrin; Hofrichter, Martin; Martínez, Ángel T. ; Gutiérrez Suárez, Ana
Issue Date15-Apr-2020
PublisherAmerican Chemical Society
CitationJournal of Agricultural and Food Chemistry 68(19): 5375-5383 (2020)
AbstractApocarotenoids are among the most highly valued fragrance constituents, being also appreciated as synthetic building blocks. This work shows the ability of unspecific peroxygenases (UPOs, EC1.11.2.1) from several fungi, some of them being described recently, to catalyze the oxyfunctionalization of α- and β-ionones and α- and β-damascones. Enzymatic reactions yielded oxygenated products such as hydroxy, oxo, carboxy, and epoxy derivatives that are interesting compounds for the flavor and fragrance and pharmaceutical industries. Although variable regioselectivity was observed depending on the substrate and enzyme, oxygenation was preferentially produced at the allylic position in the ring, being especially evident in the reaction with α-ionone, forming 3-hydroxy-α-ionone and/or 3-oxo-α-ionone. Noteworthy were the reactions with damascones, in the course of which some UPOs oxygenated the terminal position of the side chain, forming oxygenated derivatives (i.e., the corresponding alcohol, aldehyde, and carboxylic acid) at C-10, which were predominant in the Agrocybe aegerita UPO reactions, and first reported here.
Description9 páginas.- 6 figuras.- 5 tablas.- 37 referencias.- The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jafc.0c01019
Publisher version (URL)http://dx.doi.org/10.1021/acs.jafc.0c01019
Appears in Collections:(IRNAS) Artículos
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