12-Substituted-13,14-dihydroretinols designed for affinity labeling of retinol binding- and processing proteins

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• 作者：Yefidoff ; Revital ; Albeck ; Amnon
• 关键词：Retinol analogs ; Retinol binding proteins ; trans Retinyl ester isomerohydrolase ; Affinity labeling ; Michael acceptors
• 刊名：Tetrahedron
• 出版年：2004
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：September 6, 2004
• 卷：60
• 期：37
• 页码：8093-8102
• 文件大小：290 K

摘要

All-trans- and 11-cis-retinol derivatives substituted with various electron-withdrawing groups at C₁₂ 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 C₁₂ of the polyene chain. Therefore, they are expected to be highly selective towards such proteins that have a nucleophilic residue near the C₁₁ 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 C₁₂ position of the retinol skeleton.