Stereodynamic Chemosensors

OVERVIEW

Georgetown researchers have designed stereodynamic chemosensors that can be used for in situ determination of the absolute configuration, enantiomeric excess, and concentration of chiral compounds based on substrate-controlled induction of axial chirality and a dual-mode optical readout. This probe produces a distinct circular dichroism signal upon condensation with amino alcohols, which can be correlated to the substrate chirality and enantiomeric composition, while the independent fluorescence response is not enantioselective and allows quantification of the total sample amount.

BACKGROUND

The ever-increasing demand for new biologically active chiral compounds, particularly pharmaceuticals and agrochemicals, continues to nurture tremendous interest in asymmetric synthesis. The development of enantioselective reactions for the production of chiral compounds is vigorously pursued at numerous academic and industrial research laboratories, and the pace and prospect of these efforts have increased significantly during the last 20 years with the introduction of combinatorial methods. In contrast, the analysis of the amount and enantiomeric composition of chiral compounds has become a major bottleneck in the discovery process. Because a complete stereochemical analysis must reveal the absolute configuration, the enantiomeric composition, and the total concentration of a chiral compound, the development of a widely useful and practical probe that can accomplish all three tasks with high accuracy is a significant challenge in the field of organic chemistry.

Benefit

• Can reveal the absolute configuration, the enantiomeric composition, and the total concentration of a chiral compound
• Practical for High-Throughput-Screening (process occurs within minutes)
• The analysis avoids time-consuming work-up and purification steps
• Functional with minute sample amount

Market Application

The technology can accurately identify the absolute configuration, the enantiomeric composition, and the total concentration of a chiral compound

The technology can be used for High-Throughput-Screening of large numbers of samples in order to match the productivity of parallel synthesis and other combinatorial techniques.

Publications

• U.S. Patent No. 9,815,746
• “Stereodynamic chemosensor with selective circular dichroism and fluorescence readout for in situ determination of absolute configuration, enantiomeric excess, and concentration of chiral compounds”. J Am Chem Soc
  . 2013;135(33):12200-12203. doi:10.1021/ja406259p