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Characterization of Triacylglycerol Enantiomers Using Chiral HPLC/APCI-MS and Synthesis of Enantiomeric Triacylglycerols
Authors: Lísa Miroslav | Holčapek Michal
Year: 2013
Type of publication: článek v odborném periodiku
Name of source: Analytical Chemistry
Publisher name: American Chemical Society
Place: Washington
Page from-to: 1852-1859
Titles:
Language Name Abstract Keywords
cze Charakterizace enantiomerů triacylglycerolů pomocí chirální HPLC/APCI-MS a syntéza enantiomerních triacylglycerolů Tato páce se zabývá charakterizací enantiomerů triacylglycerolů pomocí chirální HPLC/APCI-MS analýzy v systémech s normálními fázemi a syntézou standardů enantiomerních triacylglycerolů triacylglycerol; enantiomer; vysokoúčinná kapalinová chromatografie; hmotnostní spektrometrie
eng Characterization of Triacylglycerol Enantiomers Using Chiral HPLC/APCI-MS and Synthesis of Enantiomeric Triacylglycerols In this work, the first systematic characterization of triacylglycerol (TG) enantiomers in real samples using chiral high-performance liquid chromatography (HPLC) with atmospheric pressure chemical ionization mass spectrometry (APCI-MS) is performed. Our chiral HPLC/APCI-MS method is based on the use of two cellulose-tris-(3,5-dimethylphenylcarbamate) columns connected in series using a gradient of hexane-2-propanol mobile phase. All TG enantiomers containing 1-8 DBs and different fatty acyl chain lengths are separated using our chiral HPLC method except for TGs having a combination of saturated and di- or triunsaturated fatty acyls in sn-1 and sn-3 positions. In our work, the randomization reaction of monoacyl TG standards is used for the preparation of all TG enantiomers and regioisomers in a mixture, while the stereospecific esterification of 1,2- or 2,3-isopropylidene-sn-glycerols by selected fatty acids is used for the synthesis of TG enantiomers. The composition of TG enantiomers and regioisomers in hazelnut oil and human plasma samples is determined. Unsaturated fatty acids are preferentially esterified in sn-2 position in hazelnut oil, while no significant preference of saturated or unsaturated fatty acyls is observed in case of human plasma sample. Fatty acids with the higher number of DBs are preferred in sn-1 position of TG enantiomers in hazelnut oil unlike to moderate sn-3 preference in human plasma. The characterization of cholesteryl esters from TG fraction of human plasma sample using our chiral HPLC/APCI-MS method is presented as well. high performance liquid-chromatography; mass spectrometry; triacylglycerols; nonaqueous reversed-phase; lipids; stereospecific analysis;

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