Synthesis of an 11-cis-locked biotinylated retinoid for sequestering 11-cis-retinoid binding proteins1
نویسندگان
چکیده
The synthesis of a seven-membered ring locked analogue of 11-cis-retinol, tethered to a cross-linking moiety on C-15 and a lysine-extended biotin on the C-3, was accomplished for its utilization as a probe to fish out retinol binding proteins that may be involved in the reisomerization of retinal from all-trans to 11-cis in the visual cycle.
منابع مشابه
Mapping the ligand binding pocket in the cellular retinaldehyde binding protein.
Retinoid interactions determine the function of the cellular retinaldehyde binding protein (CRALBP) in the rod visual cycle where it serves as an 11-cis-retinol acceptor for the enzymatic isomerization of all-trans- to 11-cis-retinol and as a substrate carrier for 11-cis-retinol dehydrogenase (RDH5). Based on preliminary NMR studies suggesting retinoid interactions with Met and Trp residues, hu...
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Cones function in constant light and are responsible for mediating daytime human vision. Like rods, cones use the photosensitive molecule 11-cis-retinal to detect light, and in constant illumination, a continuous supply of 11-cis-retinal is needed. A retina visual cycle is thought to provide a privileged supply of 11-cis-retinal to cones by using 11-cis-retinol generated in Müller cells. In the...
متن کاملSynthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins
The synthesis of (3R )-3-[Boc-Lys(biotinyl)-O ]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-O ]-all trans-retinol chloroacetate is described. These biotinylated retinoids are instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile...
متن کاملPreferential release of 11-cis-retinol from retinal pigment epithelial cells in the presence of cellular retinaldehyde-binding protein.
In photoreceptor cells of the retina, photoisomerization of 11-cis-retinal to all-trans-retinal triggers phototransduction. Regeneration of 11-cis-retinal proceeds via a complex set of reactions in photoreceptors and in adjacent retinal pigment epithelial cells where all-trans-retinol is isomerized to 11-cis-retinol. Our results show that isomerization in vitro only occurs in the presence of ap...
متن کاملRetinoid processing proteins in the ocular ciliary epithelium.
PURPOSE To identify retinoids and retinoid processing proteins in the ocular ciliary epithelium (CE), and to compare in cultured ciliary epithelial cell lines promoter activities of the cellular retinaldehyde binding protein (CRALBP) and interphotoreceptor retinoid binding protein (IRBP). METHODS Retinoid processing proteins were detected by RT-PCR, western analysis and immunocytochemistry. P...
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