邻苯二甲酸酯类半抗原的设计合成与抗原制备

Design and Synthesis of Phthalate Ester Haptens and Antigens

摘要:

以4-硝基邻苯二甲酸为原料，分别与正丁醇和2-乙基己醇发生酯化反应，再经Fe粉还原，制备2种邻苯二甲酸酯类（PAEs）半抗原4-氨基邻苯二甲酸二丁酯（1a）和4-氨基邻苯二甲酸二（2-乙基己）酯（1b），再将半抗原1b与戊二酸酐进行酰胺化反应，制备出第3种PAEs半抗原4-戊二酸单酰邻苯二甲酸（2-乙基己）酯（1c），产品结构经熔点、1H NMR和MS表征。将半抗原1a-1c分别与牛血清载体蛋白（BSA）和卵清白蛋白（OVA）偶联，制备得到6种PAEs人工抗原2a-2c和3a-3c，并用紫外吸收光谱进行分析表征。

Abstract:

Using 4-nitro phthalic acid as starting material, two phthalate ester haptens dibutyl 4-aminophthalate (1a) and di(hexan-3-yl) 4-aminophthalate (1b) were synthesized by the esterification with n-butyl alcohol and 2-ethylhexanol, respectively, and then via iron powder reduction. Then hapten 5-((3,4-bis(((2-ethylhexyl)oxy)carbonyl)phenyl)amino)-5-oxopentanoic acid (1c) was prepared by the amidation of hapten 1b and dihydro-2H-pyran-2,6(3H)-dione. Their structures were characterized by melting point, 1H NMR and MS. Then haptens 1a-1c were coupled with bovine serum albumin (BSA) and ovi albumin (OVA), respectively, and six antigens 2a-2c and 3a-3c were prepared and analyzed by ultraviolet absorption spectrum.