Quantitative Chirality and Concentration Sensing of Chiral Analytes Using Quinones, (Hetero)Aryl Isocyanates, and/or (Hetero)Aryl Isothiocyanates

OVERVIEW

Georgetown University researchers have developed an analytical method for the determination of the absolute configuration and/or the concentration/yield and/or the enantiomeric/diastereomeric composition of a chiral analyte in the sample. The method utilizes the formation of a covalent bond between a quinone, (hetero)aryl isocyanate, and/or (hetero)aryl isothiocyanate probe and an analyte in a sample. Chiroptical and/or optical spectroscopic signal techniques are used in the analysis of the probe–analyte derivatives.

BACKGROUND

In recent years, optical methods such as circular dichroism (CD) spectroscopy have become a popular, cost-effective alternative for enantiomeric ratio (er) determination. The simplicity of CD analysis combined with the possibility of fast and parallel data collection at minimal solvent usage can reduce the workload and increase sample throughput. This invention presents an inexpensive, commercially available achiral aryliso(thio)cyanate sensor that smoothly

reacts with amino and alcohol groups under mild conditions toward urea or carbamate products exhibiting characteristic UV and CD signals above 300 nm, which is used for quantitative er and concentration analysis.

Benefit

• The methods provide rapid and convenient tools for simultaneously determining the concentration as well as the enantiomeric composition and/or the diastereomeric composition and/or absolute configuration of chiral analytes.
• These methods may be particularly useful for evaluating high-throughput reactions whose desired product is chiral.
• The methods are fast and utilize inexpensive materials.

Market Application

• Methods can be used to determine the enantiomeric/diastereomeric composition of the desired product, thus indicating the stereoselectivity of the reaction.
• Methods can be used to determine the concentration of the total product and/or the desired isomer, thus indicating the overall or individual yield of the reaction.
• Methods allow for the determination of two or three of the absolute configuration, the concentration, the enantiomeric composition, and the diastereomeric composition of the analyte.
• Methods can also be used to determine the absolute configuration, the concentration, the enantiomeric composition, and the diastereomeric composition of the analyte.

Publications

Rapid organocatalytic chirality analysis of amines, amino acids, alcohols, amino alcohols and diols with achiral iso(thio)cyanate probes.DOI:10.1039/D1SC02061GChem. Sci., 2021,12, 8784-8790

Chiroptical Switching and Quantitative Chirality Sensing with (Pseudo)halogenated Quinones.Angewandte Chemie.Volume60,Issue52. December 20, 2021. Pages27031-27038.https://onlinelibrary.wiley.com/doi/10.1002/anie.202111542