Combining enzymatic hydrolysis with magnetic nanoparticles for resolution of chiral substances
Combining enzymatic hydrolysis with magnetic nanoparticles for resolution of chiral substances
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DOI：
10.1016/j.colsurfa.2018.12.042
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发表时间：
2019-03
期刊：
影响因子：
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通讯作者：
Xiaoxiao Li;Chenchen Meng;Qibin Chen;Huiling Tan;Ting Chen;Honglai Liu
中科院分区：
文献类型：
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作者：
Xiaoxiao Li;Chenchen Meng;Qibin Chen;Huiling Tan;Ting Chen;Honglai Liu
由于外消旋体都是对映体，化学结构和物理性质相似，因此其分离仍然是一个很大的挑战。在这里，我们提出了一种新的有效分离手性化合物的策略，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Fe 3 O 4纳米颗粒进行简单的磁性分离，可以实现外消旋体的完全拆分。本工作选择d-氨基酰化酶为酶，苯丙氨酸和蛋氨酸为手性模型。使用d-氨基酰化酶可以水解对映体，而对映体不能。设计并合成了磁性纳米Fe3O4@SiO2-NH 2-COOH复合材料，用于与水解氨基酸的酰胺化反应。在磁场的作用下，d-型氨基酸可以很容易地大规模分离，所得的拆分性能表明，该方法具有更高的选择性，与普通的手性分离技术相比。对映体过量（e.e.）对于外消旋N-酰基-苯丙氨酸和甲硫氨酸，其值分别为75%和98%，这仅仅依赖于所用酶的水解能力。这一结果表明，我们的方法是可行的，简单，易于放大和高效的手性拆分。这些结果表明，该策略可以提供新的机会，提高对映体和生物物质的高收率和高选择性的对映体分离性能的主机。
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 Fe3O4nanoparticles, 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 ofd-aminoacylase can hydrolyzed-enantiomer, whilel-enantiomer cannot. Magnetic nanoparticles of Fe3O4@SiO2-NH2-COOH composites were designed and synthesized for the amidation reaction with the hydrolyzedd-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.