通过协同催化在 pH 7 下选择性水解非活化芳基酯。
Selective Hydrolysis of Nonactivated Aryl Esters at pH 7 through Cooperative Catalysis.
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, United States.
出版信息
J Org Chem. 2023 Mar 3;88(5):3282-3287. doi: 10.1021/acs.joc.2c02570. Epub 2023 Feb 16.
Abstract
Most reported artificial esterases only hydrolyze highly activated substrates. We here report synthetic catalysts that hydrolyze nonactivated aryl esters at pH 7, via cooperative action of a thiourea group that mimics the oxyanion hole of a serine protease and a nearby nucleophilic/basic pyridyl group. The molecularly imprinted active site distinguishes subtle structural changes in the substrate, including elongation of the acyl chain by two carbons or shift of a remote methyl group by one carbon.
摘要
大多数报道的人工酯酶仅水解高度活化的底物。我们在此报告了合成催化剂，它们通过模拟丝氨酸蛋白酶的氧阴离子穴的硫脲基团和附近亲核/碱性吡啶基团的协同作用，在 pH 7 下水解非活化的芳基酯。分子印迹的活性位点可以区分底物中的细微结构变化，包括酰基链延长两个碳原子或远程甲基基团移动一个碳原子。
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