Synthesis of a fatty tetrahydroxyamide using peroxygenase from oat seeds

Prior work has shown that oat (Avena sativa) seeds are a rich source of lipase and peroxygenase. Partial epoxidation of the isobutyl amide derivative of α-linolenic acid with peroxygenase gave N-i-butyl-9, 10–15, 16-diepoxy-12(Z)-octadecenamide, a diepoxide product in which the epoxides reside only at the formerly external double bond positions. No amide hydrolysis occurred during the epoxidation procedure. Hydrolysis of the diepoxide gave N-i-butyl-9, 10,15,16-tetrahydroxy-12 (Z)-octadecenamide, a polyol derivative with relatively high polarity, potentially useful in developing new materials from fats and oils.