Rapid chiral assay of amino compounds using diethyl squarate

Spectrochim Acta A Mol Biomol Spectrosc. 2022 May 5:272:120871. doi: 10.1016/j.saa.2022.120871. Epub 2022 Jan 20.

Abstract

The versatility and importance of chiral compounds make it urgent to develop fast and efficient methods to detect the absolute configuration, enantiomeric excess(ee), and concentration of chiral compounds. In this study, we demonstrate that commercially available diethyl squarate can rapidly react with various types of chiral amino compounds and exhibit characteristic ultraviolet (UV) and circular dichroism (CD) signals. The UV and CD signals can determine the total concentration of the two enantiomers and ee value of the sample, respectively. The probe showed a broad substrate scope, applicable to 39 tested chiral amino compounds, including chiral amino acids, amino alcohols, and amines. Additionally, the probe accurately detected 10 samples of phenylalanine, phenylglycinol, and phenethylamine with the error range less than 8%, demonstrating the practicability of this method.

Keywords: CD spectroscopy; Chiral amino compounds; Chiral assay; Diethyl squarate; UV spectroscopy.

MeSH terms

  • Amines* / chemistry
  • Circular Dichroism
  • Cyclobutanes*
  • Stereoisomerism

Substances

  • Amines
  • Cyclobutanes
  • diethyl squarate