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Org Lett. 2019 Oct 4;21(19):8080-8084. doi: 10.1021/acs.orglett.9b03054. Epub 2019 Sep 23.

Stereochemistry of Linoleic Acid Esters of Hydroxy Linoleic Acids.

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Skaggs School of Pharmacy and Pharmaceutical Sciences , UC San Diego , 9500 Gilman Drive , La Jolla , California 92093-0934 , United States.
Clayton Foundation Laboratories for Peptide Biology , Salk Institute for Biological Studies , 10010 North Torrey Pines Road , La Jolla , California 92037-1002 , United States.


The syntheses of linoleic acid esters of hydroxy linoleic acids (LAHLAs) present in oat oil and human serum have been achieved, providing access to material for testing and the determination of the stereochemistry of the natural compounds. While 9- and 13-LAHLAs were found to be a mixture of enantiomers 15-LAHLA is generated in a single optical form in oat oil. The stereochemistry of 15-LAHLA in oat oil was found to be opposite to that reported for digalactosyldiacylglycerol that possesses an embedded 15-LAHLA.

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