Submitted to: Proceedings JOCS/AOCS World Congress
Publication Type: Abstract Only
Publication Acceptance Date: 1/5/2007
Publication Date: 5/13/2007
Citation: McKeon, T.A., Kang, S., He, X., Lin, J.T., Turner, C. 2007. Synthesis of Novel Acylglycerol Substrates for Acyltransferases.. Proceedings JOCS/AOCS World Congress. Interpretive Summary:
Technical Abstract: 1,2-Diacylglycerols (DG) are the native substrates for the diacylglycerol acyltransferase (DGAT). It is difficult to chemically synthesize DG containing hydroxy fatty acids in specific positions on the glycerol backbone. An alternate approach is to start from acylglycerols containing hydroxy fatty acids, and selectively remove fatty acid chains to obtain the desired acylglycerol. This study identified optimal parameters for lipase-catalyzed methanolysis of triricinolein to produce 1,2(2,3)-diricinolein, the substrate for biosynthesis of triricinolein in castor (Ricinus communis). Penicillium roquefortii lipase gave the highest yield of 1,2(2,3)-diricinolein and this lipase showed the highest specificity for the reaction, i.e. high selectivity for reaction with triricinolein, but low for diricinolein. The diacylglycerol produced can be acylated by the DGAT from Arabidopsis thaliana. Therefore, the product of the lipase reaction is a suitable substrate for acyltransferase reactions. We also evaluated conditions for synthesizing tri-gydroxy-stearin, using esterification of glycerol and 12-hydroxystearic acids in a solvent free system. We identified optimal parameters for lipase-catalyzed synthesis of tri-12-hydroxystearin (THS) from glycerol and 12-hydroxystearic acid (12-HSA), using Lipozyme RMIM 60 from Rhizomucor miehei (RML). We obtained yields of THS up to 75% under optimum conditions.