Design and synthesis of chiral and racemic phosphonate-based haptens for the induction of aldolase catalytic antibodies
作者:YongQi Mu、Richard A Gibbs
DOI:10.1016/s0968-0896(97)00088-6
日期:1997.7
alternative phosphonate hapten 39 was prepared. The key step in the synthesis of 39 was the direct generation of an unprotected phosphonate precursor via coupling of the secondary alcohol 37 with CH3P(O)Cl2. The chiral counterpart of hapten 39 was also synthesized from alcohol 46, prepared by Corey's asymmetric reduction method. One polyclonal antibody preparation generated from 39 appeared to catalyze the
描述了一种新的生成醛缩酶催化抗体的策略,该策略基于使用抗体催化的烯醇酯水解作为“触发”来生成反应性烯醇酸酯中间体。开发了测试该策略的模型系统,并合成了基板8。然而,靶向的双功能半抗原11和33是合成上不可及的,因此制备了替代的膦酸酯半抗原39。合成39的关键步骤是通过仲醇37与CH3P(O)Cl2的偶联直接生成未保护的膦酸酯前体。半抗原39的手性对应物也由通过Corey的不对称还原方法制备的醇46合成。一种由39生成的多克隆抗体制剂似乎可以催化仲乙酸酯49的水解,