Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale

Abstract We report here a two‐step process for the high‐yield enzymatic synthesis of 2‐monoacylglycerides (2‐MAG) of saturated as well as unsaturated fatty acids with different chain lengths. The process consists of two steps: first the unselective esterification of fatty acids and glycerol leading to a triacylglyceride followed by an sn 1,3‐selective alcoholysis reaction yielding 2‐monoacylglycerides. Remarkably, both steps can be catalyzed by lipase B from Candida antarctica (CalB). The whole process including esterification and alcoholysis was scaled up in a miniplant to a total volume of 10 l. With this volume, a two‐step process catalyzed by CalB for the synthesis of 1,3‐oleoyl‐2‐palmitoylglycerol (OPO) using tripalmitate as starting material was established. On a laboratory scale, we obtained gram quantities of the synthesized 2‐monoacylglycerides of polyunsaturated fatty acids such as arachidonic‐, docosahexaenoic‐ and eicosapentaenoic acids and up to 96.4% of the theoretically possible yield with 95% purity. On a technical scale (>100 g of product, >5 l of reaction volume), 97% yield was reached in the esterification and 73% in the alcoholysis and a new promising process for the enzymatic synthesis of OPO was established.