Stereospecificity of Retinol Saturase: Absolute Configuration, Synthesis, and Biological Evaluation of Dihydroretinoids
Copyright policy )Stereospecificity of Retinol Saturase: Absolute Configuration, Synthesis, and Biological Evaluation of Dihydroretinoids
Retinol saturase carries out a stereospecific saturation of the C13−C14 double bond of all-trans-retinol to generate (13R)-all-trans-13,14-dihydroretinol. This compound is found in cells expressing mouse or zebrafish retinol saturase and in the livers of mice fed retinyl palmitate. All-trans-13,14-dihydroretinol is oxidized in vivo to all-trans-13,14-dihydroretinoic acid, a highly selective agonist of the retinoic acid receptor. The naturally occurring (13R)-all-trans-13,14-dihydroretinoic acid is a weaker agonist than the (13S) enantiomer, indicating enantioselective recognition by the ligand-binding pocket of this receptor. Consequently the (13S) enantiomer, acting through the retinoic acid receptor, also inhibits adipose differentiation more potently than the (13R) enantiomer.
- University of Pennsylvania United States
- Case Western Reserve University United States
- Universidade de Vigo Spain
Oxidoreductases Acting on CH-CH Group Donors, Retinyl Esters, Stereoisomerism, Tretinoin, Zebrafish Proteins, Lipids, Mice, Retinoids, Gene Expression Regulation, Liver, Models, Chemical, Adipocytes, Animals, Diterpenes, Vitamin A, Dimerization, Chromatography, High Pressure Liquid, Zebrafish
Oxidoreductases Acting on CH-CH Group Donors, Retinyl Esters, Stereoisomerism, Tretinoin, Zebrafish Proteins, Lipids, Mice, Retinoids, Gene Expression Regulation, Liver, Models, Chemical, Adipocytes, Animals, Diterpenes, Vitamin A, Dimerization, Chromatography, High Pressure Liquid, Zebrafish
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