13-Demethyl-13-substituted-13,14-dihydroretinols as potential affinity labels of retinol-binding proteins: syntheses and stability studies.
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.
Yefidoff
Revital
R
Department of Chemistry, The Julius Spokojny Bioorganic Chemistry Laboratory, Bar Ilan University, Ramat Gan 52900, Israel.
Weiss
Limor
L
Avisar
David
D
Albeck
Amnon
A
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
D000345:Affinity Labels; D012177:Retinol-Binding Proteins; D014801:Vitamin A