Moor Sarah R, Howard James R, Herrera Brenden T, Anslyn Eric V
Department of Chemistry, The University of Texas at Austin, Austin, TX 78712, USA.
Tetrahedron. 2021 Aug 13;94. doi: 10.1016/j.tet.2021.132315. Epub 2021 Jul 5.
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 () of α-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 wellplate reader, the analyte is then incorporated into a three-component octahedral Fe(II) assembly for determination using an EKKO CD plate-reader. With these two assays, both the and yield of asymmetric transformations of 192 samples could be determined with acceptable errors in under fifteen minutes (not counting the preparation time). This combined speed and accuracy provides an attractive solution to overcoming analytical bottlenecks when creating α-chiral amines.
开发了一种新型筛选方案，该方案结合了荧光指示剂置换分析法和圆二色性（CD）活性Fe（II）配合物，分别用于测定α-手性胺的浓度和对映体过量（ee）。分析物浓度通过预先形成的非荧光亚胺进行定量，其中手性胺的转亚胺化作用导致荧光团2-萘胺的置换。在酶标仪中通过荧光识别胺的浓度后，将分析物加入到一个三元八面体Fe（II）组装体中，使用EKKO CD酶标仪进行ee测定。通过这两种分析方法，192个样品的不对称转化的ee和产率都可以在不到15分钟的时间内以可接受的误差确定（不包括制备时间）。这种速度和准确性的结合为克服制备α-手性胺时的分析瓶颈提供了一个有吸引力的解决方案。
