Enzymatic esterification of glycerol I. Lipase‐catalyzed synthesis of regioisomerically pure 1,3‐sn‐diacylglycerols

Abstract

Regioisomerically pure 1,3‐sn‐diacylglycerols are conveniently prepared in high yields (>80%) and in large quantities by enzymatic esterification of glycerol in the presence of various 1,3‐selective lipases(Chromobacterium viscosum, Rhizopus delemar, Rhizomucor miehei) and a variety of different acyl donors like free fatty acids, fatty acid alkyl esters and vinyl esters. All reactions are carried out in aprotic organic solvents of low water content, namelyn‐hexane, diethyl ether or tBuOMe. The creation of an artificial interphase between the solvent‐immiscible hydrophilic glycerol and the hydrophobic reaction media by the adsorption of glycerol onto a solid support prior to use was essential for the success of these transformations. The effects of reaction conditions and the regioselectivities of the lipases on the product yields are described in detail.

Synthesis of Either Mono-or Diacylglycerol from High-Oleic Sunflower Oil by Lipase-Catalyzed Glycerolysis.

“…Diacylglycerols (DAG) are also synthesized by chemical glycerolysis of edible fats and oils, and used in the processes for foods, cosmetics, etc. However, only a few papers have been published that specifically attempted a high yield of DAG using enzymatic methods (Berger et al, 1992a). The difference in the reaction conditions between MAG and DAG syntheses from high-oleic sunfiower oil by lipasecatalyzed glycerolysis is described in this work.…”

Lipase-Catalyzed Synthesis of Diacylglycerol and Monoacylglycerol from Unsaturated Fatty Acid in Organic Solvent System

“…Where as in the presence of enzymes, the same reactions may be carried out at reasonable lower temperature and atmospheric pressure without discoloration and production of undesired by-products. The use of lipolytic enzyme to catalyze the esterification reaction has been investigated by many workers (4)(5)(6)(7)(8)(9). Diacylglycerols (DAG) and Monoacylglycerols (MAG) are potentially attractive starting materials for numerous synthetic applications (10)(11).…”

Oleochemical Industry Future through Biotechnology

“…The major drawbacks of this process include high-energy consumption, low yield, and poor product quality 66 . The replacement of inorganic catalysts by lipases in the synthesis of partial glycerides has advantages of catalysis at lower temperatures which prevents the discoloration and avoids side product formation 68,69 , less polluting and energy consuming, moreover, it can produce glycerides with unsaturated fatty acids, that is commonly difficult by chemical methods.…”