Unified sensing of the concentration and enantiomeric composition of chiral compounds with an achiral probe

Abstract

•Concentration and enantiomeric ratio analysis is achieved by unified CD sensing •UV and fluorescence measurements are not needed anymore •Tested with amines, amino alcohols, amino acids, and with an asymmetric reaction •Significant speed, labor, and cost benefits at reduced chemical waste production Long-standing impracticalities with optical chiral compound sensing have limited the potential and acceptance of high-throughput experimentation technology despite the introduction of commercially available circular dichroism (CD) microplate readers. Chiroptical asymmetric reaction sensing typically requires UV or fluorescence measurements in combination with CD analysis to determine yield and enantiomeric ratio with two separate calibration curves. Herein, we introduce a strategy that achieves both through the exclusive use of CD analysis with an achiral probe designed for quantitative sensing of amines, amino alcohols, and all standard chiral amino acids, thus eliminating the need for UV and fluorescence measurements. Unified CD sensing outperforms traditional optical, NMR, and chromatographic methods and offers speed, labor, and cost benefits at reduced chemical waste production. It can be easily adapted by any laboratory, it can be applied in microscale asymmetric reaction screening without workup, and it is universally applicable and not restricted to the use of any particular optical probe. Long-standing impracticalities with optical chiral compound sensing have limited the potential and acceptance of high-throughput experimentation technology despite the introduction of commercially available circular dichroism (CD) microplate readers. Chiroptical asymmetric reaction sensing typically requires UV or fluorescence measurements in combination with CD analysis to determine yield and enantiomeric ratio with two separate calibration curves. Herein, we introduce a strategy that achieves both through the exclusive use of CD analysis with an achiral probe designed for quantitative sensing of amines, amino alcohols, and all standard chiral amino acids, thus eliminating the need for UV and fluorescence measurements. Unified CD sensing outperforms traditional optical, NMR, and chromatographic methods and offers speed, labor, and cost benefits at reduced chemical waste production. It can be easily adapted by any laboratory, it can be applied in microscale asymmetric reaction screening without workup, and it is universally applicable and not restricted to the use of any particular optical probe.