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Cholesterol molecular probe as well as preparation method and application thereof
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A technology of molecular probes and cholesterol, applied in biochemical equipment and methods, chemical instruments and methods, peptide sources, etc.
Active Publication Date: 2017-06-20
WUHAN UNIV +1
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Many studies have shown that there are new cholesterol-modified proteins, but due to the bipolar molecular characteristics of cholesterol molecules, there has been no good method for identifying cholesterol-modified proteins.
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Embodiment 1
[0109] Embodiment 1: the preparation of compound L1
[0110] Lithocholic acid (1.88g, 5.0mmol) was dissolved in anhydrousmethanol, and p-toluenesulfonic acid (100mg, 0.5mmol) was added. The reaction was carried out at room temperature for 4 hours. After the TLC detection reaction was complete, the reaction solution was concentrated, 150 mL of ethyl acetate was added, washed with saturated sodiumbicarbonate solution and saturated sodiumchloride solution respectively, dried over anhydroussodiumsulfate, concentrated, and subjected to silica gelcolumn chromatography (PE:EA=1: 1) A white solid (1.9 g, 97%) was obtained. 1 H NMR (300MHz, CDCl 3 )δ 3.66(s,3H), 3.65–3.58(m,1H), 0.92(s,3H), 0.90(s,3H), 0.64(s,3H).
Embodiment 2
[0111] Embodiment 2: the preparation of compound L2
[0112] L1 (1.8 g, 4.6 mmol) was dissolved in anhydrous DMSO (30 mL) and anhydrous toluene (30 mL), and IBX (1.7 g, 6.0 mmoL) was added. React at room temperature for 3 hours, after the reaction is complete by TLC, add water and ethyl acetate, remove insoluble matter by suction filtration, extract the filtrate with ethyl acetate, combine the organic phases, wash with a large amount of water, wash with saturated sodium chloride solution, and dry over anhydrous sodium sulfate , concentrated, and silica gelcolumn chromatography (PE:EA=2:1) gave a white solid (1.63g, 90%). 1 H NMR (300MHz, CDCl 3 ) δ 3.66 (s, 3H), 1.01 (s, 3H), 0.92 (d, J=6.3Hz, 3H), 0.68 (s, 3H).
Embodiment 3
[0113] Embodiment 3: the preparation of compound L3
[0114] Dissolve L2 (1.9g, 4.9mmol) in anhydrous DMSO, add IBX (1.7g, 6.0mmoL) and a catalytic amount of trifluoroacetic acid, stir at 40°C for 12 hours, after TLC detects that the reaction is complete, add water and ethyl acetate Insoluble matter was removed by suction filtration, the filtrate was extracted with ethyl acetate, the organic phases were combined, washed with a large amount of water, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated, and obtained by silica gelcolumn chromatography (PE:EA=2:1) White solid (855mg, 45%). 1 H NMR (300MHz, CDCl 3 )δ 5.72 (s, 1H), 3.66 (s, 3H), 1.17 (s, 3H), 0.91 (d, J=6.3Hz, 3H), 0.70 (s, 3H).
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technical field [0001] The invention belongs to the technical field of biology, medicine and its preparation and application, and specifically relates to a cholesterol molecular probe, its preparation, and its application in the process of identifying and analyzing cholesterol-modified proteins. Background technique [0002] Cholesterol modification of protein is a special post-translational modification. Since 1996, the only cholesterol-modified protein discovered is hedgehog protein. Cholesterol modification is closely related to the maturation and development of hedgehog protein and the occurrence of cancer. Many studies have shown that there are new cholesterol-modified proteins, but due to the bipolar molecular characteristics of cholesterol molecules, there has been no good method for identifying cholesterol-modified proteins. The azido-alkynyl cycloaddition reaction catalyzed by copper ions has the advantages of mild conditions and high yield, which makes up for the ...
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