Stereospecific analysis of triacyl-sn-glycerolsvia resolution of diastereomeric diacylglycerol derivatives by high-performance liquid chromatography on silica |
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Authors: | William W Christie Boryana Nikolova-Damyanova Päivi Laakso Bengt Herslof |
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Affiliation: | (1) Hannah Research Institute, KA6 5HL Ayr, Scotland;(2) Karlshamns LipidTeknik, S-104 65 Stockholm, Sweden;(3) Present address: Centre of Phytochemistry, Institute of Organic Chemistry, 1113 Sofia, Bulgaria;(4) Present address: Dept. of Chemistry and Biochemistry, Laboratory of Food Chemistry, University of Turku, 20500 Turku, Finland |
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Abstract: | The compositions of positionssn-1, 2 and 3 of triacylglycerols can be determined by partial hydrolysis with ethyl magnesium bromide, derivatization of the
total products with (S)-(+)-1-(1-naphthyl)ethyl isocyanate and isolation of the diacyl-sn-glycerol urethane derivatives by chromatography on solid-phase extraction columns containing an octadecylsilyl phase. The
diastereomericsn-1,2-and 2,3-diacylglycerol derivatives are separated by high-performance liquid chromatography on silica for determination
of their fatty acids by gas chromatography. Each step in the process has been evaluated rigorously. The compositions of all
three positions can be calculated with good accuracy from the analyses of these compounds and that of the total triacylglycerols.
Although the 1,3-sn-diacylglycerol derivatives can also be isolated easily, they do not give reliable results for the composition of positionsn-2 because acyl migration occurs during their generation. The stereospecific analysis procedure has been applied to some plant
and animal triacyl-sn-glycerols of commercial and scientific interest, containing predominantly C16 and C18 fatty acids,i.e. safflower, sunflower, olive and palm oils, tallow, egg and rat adipose tissue. The method is not at present suited to the
analysis of more complex triacylglycerols, such as milk fat or fish oils, and problems associated with these are discussed. |
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Keywords: | Chiral chromatography diacylglycerols Grignard hydrolysis high-performance liquid chromatography stereospecific analysis triacylglycerols |
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