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HPLC Resolution of Diacylglycerol Moieties of Natural Triacylglycerols on a Chiral Phase Consisting of Bonded (R)-(+)-1-(1-naphthyl)ethylamine

HPLC Resolution of Diacylglycerol Moieties of Natural Triacylglycerols on a Chiral Phase Consisting of Bonded (R)-(+)-1-(1-naphthyl)ethylamine

Y Itabashi, A Kukis, L Marai, T Takagi

J Lipid Res. 1990 Sep;31(9):1711-7.

PMID: 2246620

Abstract:

Chiral phase high performance liquid chromatographic resolution of sn-1,2(2,3)- and X-1,3-diacylglycerols generated by partial Grignard degradation from natural triacylglycerols was carried out using a chiral column (25 cm x 4.6 mm i.d.) containing (R)-(+)-1-(1-napthyl)ethylamine polymer chemically bonded to 300A wide pore spherical silica (5 microns particles). The diacylglycerols were chromatographed as 3,5-dinitrophenyl-urethanes and detected at 226 or 254 nm UV. By an isocratic elution with n-hexane- 1,2-dichloroethane-ethanol 40:10:1 (v/v/v) as the mobile phase, the sn-1,2(2,3)-diacylglycerols from corn, linseed, and menhaden oils were resolved into two clearly distinguishable enantiomer groups, although some peak overlappings between the enantiomers were observed in the linseed and menhaden oil diacylglycerols. In addition to the excellent enantiomer resolution, each enantiomer and the X-1,3-isomers were partially resolved into several peaks, which could be tentatively identified on the basis of equivalent carbon number. It is concluded that chiral phase high performance liquid chromatography can be utilized for effective resolution, identification, and quantitation of enantiomeric diacylglycerols from complex natural mixtures.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3886702	(R)-(+)-1-(1-Naphthyl)ethylamine		3886-70-2	Price

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