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Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids

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dc.contributor Háskóli Íslands
dc.contributor University of Iceland
dc.contributor.author Kalpio, Marika
dc.contributor.author Magnússon, Jóhann D.
dc.contributor.author Guðmundsson, Haraldur G.
dc.contributor.author Linderborg, Kaisa M.
dc.contributor.author Kallio, Heikki
dc.contributor.author Haraldsson, Guðmundur G.
dc.contributor.author Yang, Baoru
dc.date.accessioned 2020-11-23T13:58:08Z
dc.date.available 2020-11-23T13:58:08Z
dc.date.issued 2020-09
dc.identifier.citation Kalpio, M., et al. (2020). "Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids." Chemistry and Physics of Lipids 231: 104937.
dc.identifier.issn 0009-3084
dc.identifier.uri https://hdl.handle.net/20.500.11815/2225
dc.description Publisher's version (útgefin grein)
dc.description.abstract The stereospecific structure of triacylglycerols (TAGs) affects the bioavailability of fatty acids. Lack of enantiopure reference compounds and effective enantiospecific methods have hindered the stereospecific analysis of individual TAGs. Twelve novel enantiostructured AAB-type TAGs were synthesized containing one of the three n-3 polyunsaturated fatty acid: α-linolenic acid (ALA), eicosapentaenoic acid (EPA), or docosahexaenoic acid (DHA) in sn-1 or sn-3 position. These compounds formed six enantiomer pairs, which were separated with recycling high-performance liquid chromatography using chiral columns and UV detection. The chromatographic retention behavior of the enantiomers and the stereospecific elution order were studied. The enantiomer with an n-3 PUFA in the sn-1 position eluted faster than the enantiomer with the n-3 PUFA in the sn-3 position, regardless of the carbon chain length and number of double bonds of the PUFA. TAG enantiomers containing DHA exhibited highly different retention on the chiral column and were separated after the first column, whereas recycling was needed to separate the enantiomer pairs containing ALA or EPA. The system using two identical columns and one mobile phase, without sample derivatization, proved to be very effective also for peak purity assessment, confirming the enantiopurity of the synthesized structured TAGs being higher than 98 % (96 % ee).
dc.description.sponsorship The authors thank Jani Sointusalo at University of Turku for assistance with the recycling system, Dr. Sigridur Jonsdottir at the Science Institute, University of Iceland, for the accurate mass measurements, Novozymes AS in Denmark for the lipase and Olav Thorstad of Pronova BioPharma ASA in Norway for pure DHA. The work was funded by the Academy of Finland (Decision Nos. 310982 and 315274 ), and the Finnish Cultural Foundation . Haraldur G. Gudmundsson acknowledges financial support for a temporary postdoctoral research at University of Turku and Jóhann D. Magnússon financial support from Lýsi hf. in Iceland .
dc.format.extent 104937
dc.language.iso en
dc.publisher Elsevier BV
dc.relation.ispartofseries Chemistry and Physics of Lipids;231
dc.rights info:eu-repo/semantics/openAccess
dc.subject Chemoenzymatic synthesis
dc.subject Enantiospecific separation
dc.subject Enantiostructured triacylglycerols
dc.subject n-3 fatty acids
dc.subject Recycling liquid chromatography
dc.subject Lífefnafræði
dc.subject Fituefni
dc.title Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids
dc.type info:eu-repo/semantics/article
dcterms.license This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).
dc.description.version Peer Reviewed
dc.identifier.journal Chemistry and Physics of Lipids
dc.identifier.doi 10.1016/j.chemphyslip.2020.104937
dc.relation.url https://www.sciencedirect.com/science/article/pii/S0009308420300682?via%3Dihub
dc.contributor.department Raunvísindastofnun (HÍ)
dc.contributor.department Science Institute (UI)
dc.contributor.school Verkfræði- og náttúruvísindasvið (HÍ)
dc.contributor.school School of Engineering and Natural Sciences (UI)

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