Stereospecific Analysis of Acyl Group Distribution in Triacylglycerols by HPLC with Chiral Column

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Abstract
High-performance liquid chromatography (HPLC) using a chiral stationary phase N- (S) -2- (4-chlorophenyl) -D-isovaleroyl-D-phenylglycine chemically bound to γ-aminopropyl silanized silica (Sumipax OA 2100) was improved for the separation of homologous mixtures of saturated and unsaturated 1-monoacylglycerol (MG) enantiomers as 3, 5-dinitrophenylurethane (3, 5-DNPU) derivatives. By this HPLC method, it was possible to separate three saturated 1-MGs having consecutive even-carbon numbers, and 1-MG mixtures of 18 : 0, 18 : 1, 18 : 2, and 18 : 3 to sn-1 and sn-3 enantiomers of each component. It was used for the stereospecific analysis of acyl group distributions in triacylglycerols from linseed oil. A 1-MG sample from the degradation of TGs with Grignard reagent was fractionated to saturated and unsaturated fractions by thin layer chromatography on silver nitrate and boric acid-impregnated silicic acid plates. The total, saturated and unsaturated 1-MG samples were then analyzed as 3, 5-DNPU derivatives by HPLC on the chiral stationary phase. Acyl group distributions at the sn-1, sn-2 and sn-3 positions were determined based on the data obtained.

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