High-throughput screening of a-chiral-primary amines to determine yield and enantiomeric excess
High-throughput screening of a-chiral-primary amines to determine yield and enantiomeric excess
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DOI：
10.1016/j.tet.2021.132315
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发表时间：
2021-08-17
期刊：
影响因子：
2.1
通讯作者：
V. Anslyn, Eric
中科院分区：
文献类型：
--
作者：
Moor, Sarah R.;Howard, James R.;V. Anslyn, Eric
开发了一种新的筛选方案，使用荧光指示剂置换分析和圆二色性（CD）活性Fe（II）配合物的组合，以确定浓度和对映体过量（ee）的α-手性胺，分别。用预先形成的非荧光亚胺定量分析物浓度，其中与手性胺的transimination导致荧光团2-萘胺的置换。在通过孔板读取器中的荧光辨别胺的浓度后，然后将分析物掺入三组分八面体Fe（II）组装体中，使用EKKO CD板读取器进行ee测定。用这两种方法测定了192个样品的不对称转化的ee和产率，误差小于15 min（不计制备时间）。这种结合的速度和准确度提供了一种有吸引力的解决方案，以克服分析瓶颈时，创造α-手性胺。(c)2021爱思唯尔有限公司保留所有权利。
A novel screening protocol was developed using a combination of a fluorescent indicator displacement assay and a circular dichroism (CD) active Fe(II) complex to determine concentration and enantiomeric excess (ee) of a-chiral amines, respectively. The analyte concentration is quantified with a pre-formed non-fluorescent imine, where transimination with the chiral amine results in displacement of the fluorophore 2-naphthylamine. After discerning the concentration of amine via fluorescence in a well-plate reader, the analyte is then incorporated into a three-component octahedral Fe(II) assembly for ee determination using an EKKO CD plate-reader. With these two assays, both the ee and yield of asymmetric transformations of 192 samples could be determined with acceptable errors in under 15 min (not counting the preparation time). This combined speed and accuracy provides an attractive solution to overcoming analytical bottlenecks when creating a-chiral amines. (c) 2021 Elsevier Ltd. All rights reserved.