Journal article
Isomerization of all-(E)-Retinoic Acid Mediated by Carbodiimide Activation - Synthesis of ATRA Ether Lipid Conjugates
Department of Chemistry, Technical University of Denmark1
Organic Chemistry, Department of Chemistry, Technical University of Denmark2
Colloids and Biological Interfaces Group, Self-organizing materials for nanotechnology Section, Department of Micro- and Nanotechnology, Technical University of Denmark3
Self-organizing materials for nanotechnology Section, Department of Micro- and Nanotechnology, Technical University of Denmark4
Department of Micro- and Nanotechnology, Technical University of Denmark5
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.
| Language: | English |
|---|---|
| Year: | 2010 |
| Pages: | 719-724 |
| ISSN: | 10990690 and 1434193x |
| Types: | Journal article |
| DOI: | 10.1002/ejoc.200901128 |
| ORCIDs: | Andresen, Thomas Lars , Madsen, Robert and Clausen, Mads Hartvig |
