REGIOISOMERICALLY PURE MONOACYLGLYCEROL AND DIACYLGLYCEROL AS SYNTHETIC BUILDING-BLOCKS

Regioisomerically pure mono- and diacylglycerols are valuable, non-ionic surfactants for a multitude of applications e.g. in pharmaceutical or cosmetical industry. Furthermore they are attractive intermediates for the synthesis of more complex lipids like selectively functionalised triacylglycerols, glyco- or phospholipids. Unfortunately, this high synthetic potential of these molecules could not be exploited to any great extent so far due to the apparent lack of accessibility. Lipase-catalysed reactions often proceed with high regioselectivity. Therefore it seemed logic to investigate the potential of biocatalytic synthesis leading to the desired glycerides. The lipase-catalysed esterification of glycerol in presence of various acyl-donors (free fatty acids, fatty acid methyl esters, -vinyl esters, synthetic triglycerides, natural fats and oils) indeed provided regioisomerically pure 1,3-sn-di- and 1(3)-rac-monoacylglycerols in high yields and synthetically useful quantities. Modification of the free hydroxyl functions of the target molecules led to various, multifunctionalised C3-building blocks containing a prochiral center, selectively functionalized triacylglycerols and pharmacologically active compounds.