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Limonene is one of the most abundant naturally occurring cyclic monoterpenes and has recently emerged as a sustainable alternative to petroleum-based solvents as well as a chemical platform for the production of value-added compounds. The biocatalytic epoxidation of both enantiomers of limonene was carried out in the presence of a peroxygenase-containing preparation from oat ( Avena sativa ) flour. Different reaction profiles were observed depending on the starting enantiomer of limonene, but in both cases the 1,2-monoepoxide was obtained as the main product with excellent diastereoselectivity. Trans -1,2-monoepoxide and cis -1,2-monoepoxide were isolated from the reaction of ( R )-limonene and ( S )-limonene, respectively, and the reactions were scaled-up to 0.17 M substrate concentration. The process is valuable for operational simplicity, lack of toxic metal catalysts, and cost-effectiveness of the enzymatic source. Pure stereoisomers of 1,2-monoepoxides of limonene constitute a useful starting material for biorenewable polymers, but can be also converted into other chiral derivatives by epoxide ring opening with nucleophiles. As a proof of concept, a tandem protocol for the preparation of enantiopure (1 S ,2 S ,4 R )-1,2-diol from ( R )-limonene and (1 R ,2 R ,4 S )-1,2-diol from ( S )-limonene was developed.

Stereospecific Epoxidation of Limonene Catalyzed by Peroxygenase from Oat Seeds