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

Mikkel Stochkendahl Christensen, Palle Jacob Pedersen, Thomas Lars Andresen, Robert Madsen, Mads Hartvig Clausen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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
Issue number4
Pages (from-to)719-724
ISSN1434-193X
DOIs
Publication statusPublished - 2010

Keywords

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

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