102491-55-4Relevant academic research and scientific papers
Enantioselective chromatography in analysis of triacylglycerols common in edible fats and oils
Kalpio, Marika,Nylund, Matts,Linderborg, Kaisa M.,Yang, Baoru,Kristinsson, Bj?rn,Haraldsson, Gudmundur G.,Kallio, Heikki
, p. 718 - 724 (2015/02/02)
Enantiomers of racemic triacylglycerol (TAG) mixtures were separated using two chiral HPLC columns with a sample recycling system and a UV detector. A closed system without sample derivatisation enabled separation and identification by using enantiopure reference compounds of eleven racemic TAGs with C12-C22 fatty acids with 0-2 double bonds. The prolonged separation time was compensated for byfewer pretreatment steps. Presence of one saturated and one unsaturated fatty acid in the asymmetricTAG favoured the separation. Enantiomeric resolution, at the same time with stronger retention of TAGs,increased with increasing fatty acid chain length in the sn-1(3) position. Triunsaturated TAGs containingoleic, linoleic or palmitoleic acids did not separate. The elution order of enantiomers was determined bychemoenzymatically synthesised enantiopure TAGs with a co-injection method. The method is applicableto many natural fats and oils of low unsaturation level assisting advanced investigation of lipid synthesisand metabolism.
Synthesis of enantiopure structured triacylglycerols
Kristinsson, Bjoern,Linderborg, Kaisa M.,Kallio, Heikki,Haraldsson, Gudmundur G.
, p. 125 - 132 (2014/02/14)
The synthesis of nine enantiopure structured triacylglycerols (TAGs) of the AAB type is described, all possessing the (S)-absolute configuration. Six of them possess one saturated and two identical unsaturated fatty acyl chains, whereas the remaining three possess two identical saturated fatty acids along with one unsaturated fatty acid. The former group was synthesized by a five-step chemoenzymatic route involving a highly regioselective immobilized Candida antarctica lipase, starting from enantiopure (R)-solketal. The second group was prepared by a fully chemical five-step approach based on the same chiral precursor. Such enantiopure TAGs are strongly required as standards for the enantiospecific analysis of intact TAGs in fats and oils.
