title: 13-Demethyl-13-substituted-13,14-dihydroretinols as potential affinity labels of retinol-binding proteins: syntheses and stability studies.
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.
authors.affiliation: Department of Chemistry, The Julius Spokojny Bioorganic Chemistry Laboratory, Bar Ilan University, Ramat Gan 52900, Israel.
authors.forename: Revital
authors.initials: R
authors.lastname: Yefidoff
authors.forename: Limor
authors.initials: L
authors.lastname: Weiss
authors.forename: David
authors.initials: D
authors.lastname: Avisar
authors.forename: Amnon
authors.initials: A
authors.lastname: Albeck
mesh_terms: D000345:Affinity Labels / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D012177:Retinol-Binding Proteins / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014801:Vitamin A / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000345:Affinity Labels; D012177:Retinol-Binding Proteins; D014801:Vitamin A