title: 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 sn1,3-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.
authors.affiliation: Institute of Technical Biochemistry, University of Stuttgart, Allmandring 31, 70569 Stuttgart, Germany.
authors.forename: Jan
authors.initials: J
authors.lastname: Pfeffer
authors.forename: Andreas
authors.initials: A
authors.lastname: Freund
authors.forename: Rachid
authors.initials: R
authors.lastname: Bel-Rhlid
authors.forename: Carl-Erik
authors.initials: CE
authors.lastname: Hansen
authors.forename: Matthias
authors.initials: M
authors.lastname: Reuss
authors.forename: Rolf D
authors.initials: RD
authors.lastname: Schmid
authors.forename: Steffen C
authors.initials: SC
authors.lastname: Maurer
mesh_terms: D001671:Biochemistry / Q000379:methods; D002384:Catalysis; D004951:Esterification; D005231:Fatty Acids, Unsaturated / Q000378:metabolism; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism*; D050178:Monoglycerides / Q000096:biosynthesis*; D019301:Oleic Acid / Q000378:metabolism; D014280:Triglycerides / Q000096:biosynthesis* / Q000737:chemistry
chemical_list: D005231:Fatty Acids, Unsaturated; D005656:Fungal Proteins; D050178:Monoglycerides; D014280:Triglycerides; D019301:Oleic Acid; D008049:Lipase; C431349:lipase B, Candida antarctica; C095376:1,3-dioleoyl-2-palmitoylglycerol