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结合酶水解与磁性纳米粒子用于手性分离
Combining Enzymatic Hydrolysis with Magnetic Nanoparticles for Resolution of Chiral Substances
【Author】 Xiaoxiao Li;Chenchen Meng;Qibin Chen;State Key Laboratory of Chemical Engineering and School of Chemistry & Molecular Engineering,East China University of Science and Technology;
【机构】 化学工程联合国家重点实验室化学与分子工程学院华东理工大学;
【摘要】 目前,外消旋体的分离仍然是一个巨大的挑战,因为它们是对映体,具有相似的化学结构和物理性质。在这里,我们提出了一种有效分离手性化合物的新策略,即通过酶立体选择性水解外消旋体的单个对映体,然后使用Fe3O4纳米颗粒进行简单的磁性分离,可以实现外消旋体的完全分离。在这项工作中,选择d-氨基酰化酶作为一种水解酶,苯丙氨酸和蛋氨酸作为手性模型。使用d-氨基酰化酶可以水解d-对映异构体,而1-对映异构体则不能水解。设计并合成了Fe3O4@SiO2-NH2-COOH复合材料的磁性纳米粒子,用于与混合物中水解的d-氨基酸进行酰胺化反应。在磁场的帮助下,d-形式的氨基酸可以很容易地并且大规模地分离,所得的分离性能表明比普通的手性分离表现出更高的选择性。外消旋N-酰基-苯丙氨酸和甲硫氨酸的对映体过量(e.e.)值分别为75%和98%,其仅依赖于所用酶的水解能力。该结果表明我们的方法可行,简单,易于放大,并且具有高效的手性拆分性能。这些研究结果表明,该策略可为对映体和生物体提供一种高产率、高选择性的手性分离的机会。
【Abstract】 At present,the separation of racemates is still a great challenge,since they are enantiomers,having similar chemical structures and physical properties.Here,we proposed a new strategy for efficiently separating chiral compounds,i.e.,stereoselectively hydrolyzing the individual enantiomer of racemates via enzyme,followed by a simple magnetic separation using Fe3O4 nanoparticles,may implement a complete resolution of racemates.In this work,d-aminoacylase was selected as enzyme,and phenylalanine and methionine as chiral models.The use of d-aminoacylase can hydrolyze d-enantiomer,while l-enantiomer can not.Magnetic nanoparticles of Fe3O4@SiO2-NH2-COOH composites were designed and synthesized for the amidation reaction with the hydrolyzed d-amino acids from the mixture.With the help of a magnetic field,d-form amino acids can be readily separated at a large scale and the resultant resolving performances indicated that this method exhibited a higher selectivity,compared with common chiral separation techniques.The enantiomeric excess (e.e.) values are 75%and 98%for racemic N-acyl-phenylalanine and methionine,respectively,which solely rely on the hydrolysis capability of used enzymes.This result suggests that our method is feasible,simple,easy to scale-up and high-efficient for the chiral resolution.These findings demonstrate that this strategy could provide new opportunities for improving enantioseparation performances for a host of enantio-and bio-substance with both high-yield and high-selectivity.
【Key words】 Enantioseparation; Magnetic nanoparticles; Enzymatic hydrolysis; Chiral resolution;
- 【会议录名称】 中国化学会第十七届全国胶体与界面化学学术会议论文(摘要)集(第二卷)
- 【会议名称】中国化学会第十七届全国胶体与界面化学学术会议
- 【会议时间】2019-07-28
- 【会议地点】中国江苏无锡
- 【分类号】TB383.1;O652.6
- 【主办单位】中国化学会