All-trans- and 11-cis-retinol derivatives substituted with various electron-withdrawing groups at C 12 were designed to be affinity labels for retinol binding and processing proteins. Unlike other non-selective highly reactive affinity labels, these compounds carry a Michael acceptor type substitution at C 12 of the polyene chain. Therefore, they are expected to be highly selective towards such proteins that have a nucleophilic residue near the C 11 position of their retinol ligand. The synthetic route for these compounds is based on the Emmons-Horner reaction of a C15 aldehyde with an appropriate phosphonate bearing the desired electron-withdrawing group to be incorporated at the C 12 position of the retinol skeleton. Graphical abstract
Bibliographical noteFunding Information:
This research was supported by a United States-Israel Binational Science Foundation grant no. 2000390.
- Affinity labeling
- Michael acceptors
- Retinol analogs
- Retinol binding proteins
- trans Retinyl ester isomerohydrolase