Sialic acid oligosaccharide-quantum dot conjugate, its preparation method and use
A technology of sialic acid oligosaccharides and quantum dots, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of expensive chips, high requirements for experimental conditions, and not being widely used.
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[0175] Unless otherwise specified, the methods used in the present invention below are conventional methods; the materials and reagents used can be obtained from commercial sources.
[0176] Reagents used below
[0177] Tris-HCl buffer solution (100 mM, pH 8.0): Tris was dissolved in water at a final concentration of 12.1 g / L, and the pH was adjusted to 8.0 with HCl.
[0178] PBS buffer (10 mM, pH 7.4): NaH 2 PO 4 0.24g / L, Na 2 HPO 4 1.42g / L, KCl 0.2g / L and NaCl 8.0g / L, the solvent is water.
[0179] Borate buffer solution (10mM, pH 7.4): boric acid 0.62g / L, borax 3.81g / L, solvent is water. The strain information for the influenza virus used below is as follows:
[0180] Strain A / California / 04 / 2009 (H1N1): Ca04H1N1 for short, literature: W.Zhang, J.Qi, Y.Shi, Q.Li, F.Gao, Y.Sun, X.Lu, Q.Lu, C.J. Vavricka, D. Liu, J. Yan, G.F. Gao, Protein Cell 2010, 1, 459–467. The Genbank number of the amino acid sequence of the HA protein is ACP41105.1; it is known that the recepto...
preparation example 1
[0183] Synthesis of Preparation Example 1 Linker
[0184] Synthesize N first 3 CH 2 (CH 2 OCH 2 ) 5 CH 2 NH 2 , and its synthesis path is as follows:
[0185]
[0186] Synthesis of Compound 1: In a 250ml round bottom flask, hexapolyethylene glycol (1.51g, 5.0mmol) was dissolved in 100mL of dry dichloromethane, followed by triethylamine (3.4mL, 25.0mmol), ice-bathed , slowly added p-toluenesulfonyl chloride (2.4g, 15.0mmol), stirred at room temperature for 26h. TLC monitored the completion of the reaction. Add 200mL of dichloromethane to dilute, then wash with 1M HCl, saturated NaHCO 3 And each 500mL of saturated NaCl washes, collects the organic phase, passes through anhydrous NaCl 2 SO 4 After drying, filtering, and evaporation of the solvent, the concentrate was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 1:2) to obtain compound 1 as a colorless oil (2.5 g, yield 87.0%). 1 H NMR (400MHz, CDCl 3 ): δ=7.79(d, J=8...
preparation example 2
[0192] Preparation Example 2 Synthesis of sialooligosaccharide and linker part
[0193] (1) Synthesis of Compound 7:
[0194]
[0195] Synthesis of Compound 5: Add acetic anhydride (62mL, 660mmol), D-lactose (25g, 73mmol) and anhydrous sodium acetate (24g, 292mmol) into a 250mL three-necked flask, and heat to 95-100°C under nitrogen protection , a clear solution was obtained. The solution was heated to reflux and reacted for 2-3h. The completion of the reaction was monitored by TLC. The reaction solution was poured into crushed ice and stirred vigorously for 2 h. A viscous paste was precipitated, filtered, extracted with ethyl acetate (3×100 mL), precipitated and combined with the organic phase and washed with saturated NaHCO 3 , water and saturated NaCl were washed three times each, and the obtained solution was dried over anhydrous sodium sulfate, concentrated and then recrystallized with ethanol to obtain a white yellowish solid 5 (42.6 g, yield 86%).
[0196] Synthes...
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