Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins
نویسندگان
چکیده
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 isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Horner–Wadsworth–Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings. q 2002 Elsevier Science Ltd. All rights
منابع مشابه
Synthesis of an 11-cis-locked biotinylated retinoid for sequestering 11-cis-retinoid binding proteins1
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.
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