Synthesis of enantiopure ABC-type triacylglycerols

The synthesis of twelve enantiopure structured triacylglycerols (TAGs) of the ABC type possessing three different fatty acids is described by a six-step chemoenzymatic approach starting from (S)-solketal. Eight of the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-...

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Veröffentlicht in:Tetrahedron 2020-01, Vol.76 (2), p.130813, Article 130813
Hauptverfasser: Gudmundsson, Haraldur G., Linderborg, Kaisa M., Kallio, Heikki, Yang, Baoru, Haraldsson, Gudmundur G.
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Sprache:eng
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Zusammenfassung:The synthesis of twelve enantiopure structured triacylglycerols (TAGs) of the ABC type possessing three different fatty acids is described by a six-step chemoenzymatic approach starting from (S)-solketal. Eight of the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-2 positions with an unsaturated fatty acyl group in the remaining sn-3 position of the glycerol skeleton, whereas the remaining four possess two different saturated acyl groups in the terminal sn-1 and sn-3 positions with an unsaturated acyl group in the sn-2 position. The former group was synthesised by a six-step chemoenzymatic route involving a highly regioselective immobilised Candida antarctica lipase. The second group was prepared by a similar six-step approach, that required two separate lipase steps. Such enantiopure TAGs are strongly demanded as standards for enantiospecific analysis of intact TAGs in fats and oils. [Display omitted] •Twelve enantiostructured ABC type triacylglycerols (TAGs) were synthesised.•Unique TAGs as standards for chiral separation.•Facile methodology to synthesise both enantiomers of ABC type TAGs.•Highly regioselective lipase.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.130813