Characterization of triacylglycerol enantiomers using chiral HPLC/APCI-MS and synthesis of enantiomeric triacylglycerols
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
23298510
DOI
10.1021/ac303237a
Knihovny.cz E-zdroje
- MeSH
- atmosférický tlak * MeSH
- hmotnostní spektrometrie metody MeSH
- lidé MeSH
- stereoizomerie MeSH
- triglyceridy chemická syntéza chemie MeSH
- vysokoúčinná kapalinová chromatografie metody MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- triglyceridy MeSH
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.
Citace poskytuje Crossref.org
Separation of enantiomeric triacylglycerols by chiral-phase HPLC