Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 5/17/2012
Publication Date: 8/23/2012
Citation: Compton, D.L., Laszlo, J.A., Appell, M.D., Vermillion, K., Evans, K.O. 2012. 2-monoacylglycerol acyl migration: Affect of fatty acid desaturation [abstract]. American Chemical Society. AGFD 127.
Technical Abstract: 2-Monoacylglycerols (2-MAG) are key synthetic intermediates used for the synthesis of ABA-type triacylglycerols where B is a highly unsaturated fatty acid at the glycerol sn-2 position and A are medium-chain saturated fatty acids at the glycerol sn-1,3 position. ABA-type structured lipids are an integral part of research conducted to understand human physiological effects of the gut, liver, and brain. This research investigated the affect of desaturation on spontaneous acyl migration of unsaturated 2-MAG. Density functional modeling of C18:1, C18:2, and C18:3 2-MAG predicted that desaturation had little effect on acyl migration, yielding activation energies of 36.26, 35.65, and 37.18 kJ mol-1, respectively, all of which were within the error of calculation, 4.18 kJ mol-1. 1H NMR kinetic measurements yielded relative energies of activation two fold higher than the predicted values, 73.3, 68.0, and 72.9 kJ mol-1, respectively, but confirmed that desaturation had very little effect on acyl migration rates.