人工抗原苯并芘的化学合成与分析

以苯并芘（benzo(a)pyrene，BaP）为起始反应物，通过碘代、Heck偶联两步化学反应合成苯并芘的羰基衍生物，再经肟化反应将羰基羧基化，采用活化酯法将羧基化半抗原与载体蛋白（牛血清蛋白）进行偶联，制备苯并芘的人工抗原。采用红外光谱（infrared spectroscopy，IR）、核磁共振波谱（nuclear magnetic resonancespectrum，NMR）和质谱（mass spectrometer，MS）对苯并芘中间产物进行表征，并用紫外扫描的方法对人工抗原进行鉴定。本实验成功羧化了苯并芘，并成功构建人工抗原，苯并芘与载体蛋白的偶联比为28∶1。

Synthesis and Analysis of Benzo(a)pyrene Artificial Antigen

Carbonyl derivatives of benzo(a)pyrene were synthesized through two-step chemical reactions of iodination and
Heck, and then their carbonyl groups were carboxylated by oximation reaction. The carboxylated haptens were conjugated
with the carrier protein, bovine serum albumin (BSA), using activated ester method for preparation of artificial antigen of
benzo(a)pyrene. In this work, the intermediate products including benzo(a)pyren-6-yl-substituted carboxylic acids (carboxyl
hapten) and 6-iodobenzoa]pyrene were characterized by infrared spectroscopy (IR), mass spectrometry (MS), and nuclear
magnetic resonance spectroscopy (NMR), and the artificial antigen was qualitatively analyzed by UV spectrophotometry.
The results indicated that the carboxylated haptens and theartificial antigen were successfully synthesized, and the coupling
ratio between carboxylated hapten and BSA was 28:1.