Isomerization of all-(E)-Retinoic Acid Mediated by Carbodiimide Activation - Synthesis of ATRA Ether Lipid Conjugates

Publication: Research - peer-reviewJournal article – Annual report year: 2010

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Treatment of the lysolipid 1-O-hexadecyl-sn-phosphatidylcholine with all-(E)-retinoic acid, DCC and DMAP resulted in poor acylation and caused (Z)/(E) isomerization of the alpha-beta double bond. In the presence of a proton source, the carbodiimide-activated all-(E)-retinoic acid undergoes fast isomerization to give a final mixture of (13E)/(13Z) isomers in a 3:1 ratio. Similar treatment of (13Z)-retinoic acid leads to the same isomer ratio. The isomerization was circumvented successfully by using a Mitsunobu reaction, which provided an efficient synthesis of all-(E)-retinoic acid sn-2-conjugated to phosphatidylcholine and phosphatidylglycerol etherlipids.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Publication date2010
Issue4
Pages719-724
ISSN1434-193X
DOIs
StatePublished
CitationsWeb of Science® Times Cited: 6

Keywords

  • Retinoic acid, Acylation, Isomerization, Mitsunobu reaction, Phospholipids
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