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Enantiomeric Separation of Asymmetric Triacylglycerol by Recycle High-Performance Liquid Chromatography With Chiral Column

Enantiomeric Separation of Asymmetric Triacylglycerol by Recycle High-Performance Liquid Chromatography With Chiral Column

Toshiharu Nagai, Hoyo Mizobe, Ikuko Otake, Kenji Ichioka, Koichi Kojima, Yumiko Matsumoto, Naohiro Gotoh, Ikuma Kuroda, Shun Wada

J Chromatogr A. 2011 May 20;1218(20):2880-6.

PMID: 21429494

Abstract:

In our previous studies, we employed recycle HPLC for the separation of triacylglycerol (TAG)-positional isomers (PIs). In this study, a recycle HPLC system equipped with a polysaccharide-based chiral column was applied to the enantiomeric separation of some asymmetric TAGs having straight-chain C16-C18 acyl residues. As a result, 1,2-dipalmitoyl-3-oleoyl-rac-glycerol (rac-PPO), 1,2-dioleoyl-3-palmitoyl-rac-glycerol (rac-OOP), and 1,2-dipalmitoyl-3-linoleoyl-rac-glycerol (rac-PPL) were resolved into their respective enantiomers. However, neither 1,2-dioleoyl-3-linoleoyl-rac-glycerol (rac-OOL), consisting of only unsaturated fatty acids, nor 1,2-dipalmitoyl-3-stearoyl-rac-glycerol (rac-PPS), consisting of only saturated fatty acids, was resolved. These results suggest that the asymmetric TAGs, used in this study, having both a palmitic acid moiety and an oleic acid (or a linoleic acid) moiety at the sn-1 or sn-3 positions are resolved by the chiral column. This new chiral separation method can be used in combination with atmospheric pressure chemical ionization mass spectrometry to determine the sn-OOP/sn-POO ratio in palm oil. This method is applicable for the chiral separation of asymmetric TAGs in palm oil.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2190207	1,2-Dioleoyl-3-linoleoyl-rac-glycerol		2190-20-7	Price
AP2190309	1,2-Dioleoyl-3-palmitoyl-rac-glycerol		2190-30-9	Price

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