Chiral Discrimination of Acyclic Secondary Amines by 19F NMR

作者：Gu, Guangxing; Zhao, Chong; Zhang, Wei; Weng, Jiajin; Xu, Zhenchuang; Wu, Jian; Xie, Yingbo; He, Xiao^*; Zhao, Yanchuan^*

来源：Analytical Chemistry, 2024, 96(2): 730-736.

DOI：10.1021/acs.analchem.3c03846

• SEPARATION
• PROBES

Chiral aliphatic amine compounds exhibit a range of physiological activities, making them highly sought-after in the pharmaceutical industry and biological research. One notable obstacle in studying these compounds stems from the pronounced steric hindrance surrounding the nitrogen atom. This characteristic often leads to a weak affinity of acyclic secondary amines for molecular probes, making their chiral discrimination intricate. In response to this challenge, our research has unveiled a novel F-19-labeled probe adept at recognizing and distinguishing between enantiomers of these acyclic secondary amines. By strategically incorporating a single fluorine atom as the F-19 label, we have managed to diminish the steric hindrance at the binding site. This alteration bolsters the probe's affinity toward bulkier analytes. As a testament to its effectiveness, we have successfully employed our probe in the chiral analysis of relevant pharmaceuticals, accurately determining their enantiocomposition.

• 单位
  中国科学院研究生院