Kariapper F Safia, Miccolis Flavia, Pilicer Samantha L, Wolf Christian
Department of Chemistry, Georgetown University, Washington, DC, USA.
Chirality. 2024 Nov;36(11):e70002. doi: 10.1002/chir.70002.
Isatins are extensively researched compounds with diverse applications, particularly as synthetic precursors in pharmaceutical developments. However, their use as optical probes for enantioselective sensing of chiral amines has not been explored to date. Herein, we present a novel chiroptical assay with an optimized isatin that generates strong, red-shifted circular dichroism (CD) signals at approximately 380 nm upon ketimine formation with chiral amines. The intensity of the induced CD signal increases linearly with the enantiomeric excess of the analyte and thus allows quantitative chirality analysis. The general usefulness of this approach is demonstrated with a broad range of aliphatic and aromatic chiral amines, and by accurate determination of the enantiomeric composition of 10 samples.
异吲哚酮是一类经过广泛研究的化合物，具有多种应用，特别是作为药物开发中的合成前体。然而，迄今为止，它们作为手性胺对映选择性传感的光学探针的用途尚未得到探索。在此，我们展示了一种新型的手性光学测定法，该方法使用了一种经过优化的异吲哚酮，它在与手性胺形成酮亚胺时，在约380nm处产生强烈的、红移的圆二色性（CD）信号。诱导CD信号的强度与分析物的对映体过量呈线性增加，因此可以进行定量手性分析。通过一系列脂肪族和芳香族手性胺以及对10个样品对映体组成的准确测定，证明了该方法的普遍实用性。
