Highly efficient enzymatic synthesis of 2-monoacylglycerides and structured lipids and their production on a technical scale.
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.
Pfeffer
Jan
J
Institute of Technical Biochemistry, University of Stuttgart, Allmandring 31, 70569 Stuttgart, Germany.
Freund
Andreas
A
Bel-Rhlid
Rachid
R
Hansen
Carl-Erik
CE
Reuss
Matthias
M
Schmid
Rolf D
RD
Maurer
Steffen C
SC
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
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