13-Demethyl-13-substituted-13,14-dihydroretinols as potential affinity labels of retinol-binding proteins: syntheses and stability studies

Revital Yefidoff; Limor Weiss; David Avisar; Amnon Albeck

doi:10.1016/j.bioorg.2003.09.002

13-Demethyl-13-substituted-13,14-dihydroretinols as potential affinity labels of retinol-binding proteins: syntheses and stability studies

Bioorg Chem. 2004 Feb;32(1):38-50. doi: 10.1016/j.bioorg.2003.09.002.

Authors

Revital Yefidoff¹, Limor Weiss, David Avisar, Amnon Albeck

Affiliation

¹ Department of Chemistry, The Julius Spokojny Bioorganic Chemistry Laboratory, Bar Ilan University, Ramat Gan 52900, Israel.

PMID: 14700561
DOI: 10.1016/j.bioorg.2003.09.002

Abstract

13-Demethyl-13-substituted-13,14-dihydroretinols were synthesized and their stability under various conditions was measured in order to evaluate whether they would be useful as affinity labels of retinol binding proteins and retinol metabolizing enzymes. The 13-chloro analog could not be isolated because it eliminated HCl under the Wittig reaction conditions of its preparation. The trans- and cis-13,14-epoxy analogs are stable in non-protic organic solvents, but undergo an elimination reaction under various chromatographic conditions and in mixtures of organic solvents with water or alcohol. The 13-hydroxy and 13-methoxy analogs are stable in aqueous solutions and are therefore suitable for biological studies.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Affinity Labels* / chemical synthesis
Affinity Labels* / chemistry
Molecular Structure
Retinol-Binding Proteins / chemistry*
Structure-Activity Relationship
Vitamin A / analogs & derivatives*
Vitamin A / chemistry

Substances

Affinity Labels
Retinol-Binding Proteins
Vitamin A