A1 Refereed original research article in a scientific journal
Synthesis of enantiopure structured triacylglycerols
Authors: Björn Kristinsson, Kaisa M. Linderborg, Heikki Kallio, Gudmundur G. Haraldsson
Publication year: 2014
Journal: Tetrahedron: Asymmetry
Journal name in source: Tetrahedron Asymmetry
Volume: 25
Issue: 2
First page : 125
Last page: 132
Number of pages: 8
ISSN: 0957-4166
DOI: https://doi.org/10.1016/j.tetasy.2013.11.015
Web address : http://api.elsevier.com/content/abstract/scopus_id:84893057235
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. © 2013 Elsevier Ltd. All rights reserved.