Chiral separation of glycerolipids by high-performance liquid chromatography

Abstract

SummarySince the enantiomer resolution of synthetic mono-and diacylglycerols as 3,5-dinitrophenylurethanes was achieved by chiral-phase high-performance liquid chromatography (HPLC) in the 1980s, the methodology has been extended to the resolution of various synthetic and naturally occurring chiral glycerolipids. The recent development of polysaccharide-based chiral stationary phases along with optimized chromatographic elution conditions has permitted direct enantiomer resolution of mono-, di-, and triacylglycerols without previous derivatization. However, there are still some compounds for which enantiomer resolution is difficult to achieve, such as phosphatidylcholine and phosphatidylethanolamine. With the development of new derivatization reagents and chromatographic techniques, resolution of these difficult compounds may be possible in the near future. Chiral-phase HPLC will become considerably important in the future as a valuable tool for further expansion of the field of lipidomics and a better understanding of lipid metabolism.

Direct separation of the diastereomers of phosphatidylcholine hydroperoxide bearing 13-hydroperoxy-9Z,11E-octadecadienoic acid using chiral stationary phase high-performance liquid chromatography

“…However, enantiomers of phospholipids such as PC and phosphatidylethanolamine (PE) are difficult to resolve via LC. Satisfactory resolution has yet to be achieved, although a partial resolution of racemic PC had been obtained on CHIRALPAK ID (amylose tris (3-chlorophenylcarbamate) immobilized to silica) using acetonitrilemethanol-diethylamine (85:15:0.1, v/v/v) as the mobile phase [30]. As shown in Fig.…”

“…Thus, we synthesized PCOOH with Rconfiguration at sn-2 carbon atom of glycerol backbone by using commercial Lyso PC (R-configuration) as a starting material. As reviewed in detail by Itabashi [30], glycerol and common fatty acids are achiral compounds that have no chiral centers in their molecules, while glycerolipids become chiral while glycerolipids become chiral when different fatty acids are bound to the sn-1 and sn-3 positions of glycerol backbone or when the sn-2 position becomes a chiral center. Almost all naturally occurring glycerolipids are chiral and can exist as both enantiomers and diastereomers.…”

Separation of Enantiomeric Triacylglycerols by Chiral‐Phase HPLC

“…The latter two are considered essential FA for humans. Chiral chromatography of TAG containing these predominantly C18 acids has been described several times [15,[25][26][27]; the most detailed study was published by Lisa and Holcapek [14], who analyzed more than 120 TAG.…”

Regioisomeric and enantiomeric analysis of triacylglycerols

“…Hexane-2-propanol or methanol can be used as a mobile phase [57]. In the case of the enantiomers it is always necessary to obtain a standard of at least one of the two possible enantiomers, because the order of elution from the column is practically impossible to predict.…”