5-methylmorpholine-3-amino-2-oxazolidone antigen and 5-methylmorpholine-3-amino-2-oxazolidone antibody, and preparation methods and applications thereof
A technology of methylmorpholine and oxazolidinone, which is applied in the field of drug detection, can solve problems such as unfavorable specific antibodies, and achieve the effects of low cost, good application prospects, and simple synthesis process
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Embodiment 1
[0056] Example 1: Synthesis of 5-methylmorpholine-3-amino-2-oxazolidinone hapten Ia
[0057]
[0058]
[0059] At 0°C, compound 1 (19.4g, 0.1mol) and 33ml (2.4equiv) trifluoroacetic anhydride were placed in a 100mL single-necked round bottom flask, and the mixture was stirred at 0°C for 1 hour and at room temperature for 3 hours. Then the trifluoroacetic anhydride was evaporated to dryness, and the excess solvent was removed by oil pump vacuum. 21 ml (2.0 equiv) of benzyl alcohol was added to the remaining oil, and the mixture was stirred at room temperature for 3 hours. The mixture was poured into 500ml of ethyl acetate, extracted with saturated sodium bicarbonate solution (100ml*4), and the aqueous phase was combined; the aqueous phase was washed once with ethyl acetate (100ml), then adjusted to pH 2, and washed with ethyl acetate ( 100ml*3) Extraction. The organic phases were combined, dried, and the solvent was evaporated to dryness to obtain 19.3 g (86% yield) of ...
Embodiment 2
[0065] Example 2: Synthesis of 5-methylmorpholine-3-amino-2-oxazolidinone hapten Ib
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[0067] Intermediate 6 (200 mg, 0.001 mol) prepared in Example 1 was dissolved in 10 ml of acetonitrile, triethylamine (0.56 ml, 0.004 mol) and a catalytic amount of DMAP were added thereto under stirring, and maleate was added to the mixture. Anhydride (196 mg, 0.001 mol). The reaction was stirred at room temperature for two hours, purified by preparative high-performance liquid chromatography, and 15 mg (5% yield) of a white solid was obtained after lyophilization, and the final product was subjected to mass spectrometry (such as figure 2 ) to identify the correct structure, thereby preparing the purified hapten Ib.
Embodiment 3
[0068] Embodiment 3: the synthesis of artificial antigen
[0069] The invention provides a preparation method of 5-methylmorpholine-3-amino-2-oxazolidinone artificial antigen, which mainly includes the synthesis of immunogen and coater. The difference between the preparation of the immunogen and the coating source lies in the type of carrier, and the carrier used in the immunogen is bovine serum albumin (BSA), α-amylase, phycocyanin, concanavalin A (ConA); The carrier protein used in the coating source is ovalbumin (OVA). Methods of Immunogen Preparation. The method for synthesizing the immunogen / enveloping agent used in the present invention is the active ester method.
[0070] (1) Synthesis of immunogen
[0071] Dissolve 15.0 mg (0.05 mmol) of the 5-methylmorpholine-3-amino-2-oxazolidinone hapten Ia described in Example 1 in 1.5 mL of DMF, stir and add 24.8 mg of DCC and 13.8 mg of NHS at 4° C. The reaction was stirred overnight under magnetic force, and the supernatant ...
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