Chromatographic separation of triacylglycerol (TG) enantiomers is a highly challenging task of analytical chemistry because of the similar physicochemical properties. The analysis of chiral TGs is crucial for improving the knowledge of lipid biochemistry and for understanding the nutritional properties of fats and oils. Thus, this study aimed to systematically investigate the chiral resolution of TGs consisting of three different fatty acyls (FAs).
View Article and Find Full Text PDFThe asymmetric synthesis of polyunsaturated triene C18:3 n-3 and C18:3 n-6 methoxylated ether lipids (MEL) of the 1--alkyl--glycerol type is described as possible structural candidates for a triene C18:3 MEL of an unknown identity found in a mixture of shark and dogfish liver oil. Their C18:3 hydrocarbon chains constitute an all- methylene skipped n-3 or n-6 triene framework, along with a methoxyl group at the 2'-position and -configuration of the resulting stereogenic center. The methoxylated polyenes are attached by an ether linkage to the hydroxymethyl group of the glycerol backbone.
View Article and Find Full Text PDFThe first total synthesis of a docosahexaenoic acid (DHA)-like methoxylated ether lipid (MEL) is reported. This compound constitutes an all- methylene skipped hexaene framework identical to that present in DHA, the well-known omega-3 polyunsaturated fatty acid. The polyene C22 hydrocarbon chain, bearing a methoxyl group in the 2-position and -configuration at the resulting chiral center, is attached by an ether linkage to the hydroxymethyl group (-1 position) of a glycerol backbone.
View Article and Find Full Text PDFThe report describes the preparation and use of a double-C3 building block intended as a head group synthon in the synthesis of saturated, mono-, and polyunsaturated 1--alkyl--glycerol type methoxylated ether lipids (MELs). The resulting head piece, an enantiopure isopropylidene-protected glyceryl glycidyl ether diastereomer, was accomplished in 49% yield (max 50%) from a 1:1 diastereomeric mixture obtained from -solketal and racemic epichlorohydrin after treatment with the Jacobsen (,)-Co(III)salen catalyst for the hydrolytic kinetic resolution of terminal epoxides. The diol hydrolytic product obtained in 47% yield from the unwanted diastereomer was reconverted into epoxide with an inversion of configuration in a three-step operation involving a highly regioselective lipase.
View Article and Find Full Text PDFLaeknabladid
December 2021
Objectives: The aim of the study was to assess the long-term effects of burn injury on the health-related quality of life of adult burn survivors in Iceland and to validate the translated Icelandic version of the Burn Specific Health Scale-Brief (BSHS-B).
Materials And Methods: The participants of this descriptive cross-sectional study were all burn survivors, 18 years or older, admitted to hospital for 24 hours or more because of skin burn during a 15 years period (N=196). They completed questionnaire about their health (BSHS-B), health related quality of life (EQ-5D-5) and additional questions on burn-related symptoms and their burn experience.