Enzymatic synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol

1,3-Dicapryloyl-2-eicosapentaenoylglycerol (CEC) was synthesized by interes terification of trieicosapentaenoylglycerol (EEE) with ethyl caprylate (EtC ) catalyzed by Lipozyme(TM). After some of the reaction conditions were opt imized, the maximal molar content of CEC in the glycerides of the reaction mixture was 91%. Among the parameters studied in the optimization, the crit ical ones were: (i) the water content, which influenced the conversion of E EE to CEC and 1-capryloyl-2-eicosapentaenoylglycerol (CEOH), and (ii) the t iming of water removal under reduced pressure for the reesterification of C EOH to form CEC. The complete synthesis of CEC from ethyl eicosapentaenoate (EtE) was performed in three steps: (i) hydrolysis of BE to free eicosapen taenoic acid (EPA), (ii) esterification of glycerol with EPA to form EEE, a nd (iii) interesterification of EEE with Etc under the optimized conditions . The first two steps were catalyzed by Novozym(TM) and the third by Lipozy me(TM). The total yield over all the steps was 88%, and no purification of the intermediates was necessary. The regioisomeric purity of the product wa s 100% by silver-ion high-pressure liquid chromatography.