Chemo-enzymatic epoxidation of fatty compounds – Focus on processes involving a lipase-catalyzed perhydrolysis step

¹ CIRAD, UMR 1208 IATE, Montpellier, F-34398 France
² Montpellier SupAgro, UMR 1208 IATE, Equipe Biotechnologie microbienne et enzymatique des lipides et des agropolymères, 2 Place Viala, F-34060 Montpellier cedex 1, France

^* Eric.Dubreucq@supagro.inra.fr
^** Pierre.Villeneuve@cirad.fr

Abstract

At the industrial scale, the chemical Prileshajev reaction is currently the only method applied to produce epoxidized plant oils. Using enzymes could be an alternative way allowing an environmentally benign and more selective epoxidation reaction. P450 monooxygenases, diiron-center oxygenases, lipoxygenases, peroxygenases, and hydrolases performing perhydrolysis are enzyme classes involved in free fatty acid and glyceride epoxidation. After a brief description of these biocatalysts, this review focuses on the chemo-enzymatic epoxidation of unsaturated fatty acyd chains, where a lipase-catalyzed peroxy acid formation is followed by an uncatalyzed “self-epoxidation”. The molecular bases of lipase-catalyzed perhydrolysis as well as the different parameters influencing the epoxidation reaction are reviewed and described in details.