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Chemoenzymatic synthesis of symmetrically structured triacylglycerols possessing short-chain fatty acids
Authors:Carlos D Magnusson
Institution:Science Institute, University of Iceland, Dunhaga 3, 107 Reykjavik, Iceland
Abstract:Synthesis of symmetrically structured triacylglycerols possessing bioactive n−3 polyunsaturated fatty acids (eicosapentaenoic acid or docosahexaenoic acid) at the 2-position and a short-chain fatty acid (C2, C4, C6) located at the end-positions by a highly efficient two-step chemoenzymatic process is described. Full regiocontrol devoid of any acyl-migration side reactions was obtained in both a lipase promoted step to introduce the short-chain fatty acids exclusively into the primary alcohol positions of glycerol using activated vinyl esters at low temperature and a subsequent coupling reaction involving free EPA and DHA using EDAC as a coupling agent.
Keywords:Lipase regioselectivity  Structured triacylglycerols  Regiocontrol  n&minus  3 PUFA
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