Apocarotenoids 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.
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