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5,6-Epoxidation of All-trans-retinoic Acid with Soybean Lipoxygenase-2 and -3.

Cooxidation activity of highly purified soybean lipoxygenase-2 and -3 was investigated with all-trans-retinoic acid as a co-substrate. Both the isoenzymes rapidly degraded retinoic acid in the presence of linoleic acid, but lipoxygenase-2 had more cooxidation activity than lipoxygenase-3. During cooxidation, 5, 6-epoxyretinoic acid was formed as a major product. HPLC on a chiral phase (Ceramospher Chiral RU-1) found a racemic mixture of the epoxide, indicating its formation by oxidative attack by peroxyl radicals.