Determining Stereoisomeric Excess and/or Concentration and/or Absolute Configuration of Chiral Compounds In a Sample

Categories: “Medical and Research Devices“

Reference #: 2014-016

OTC Contact: Sharon E. Pula, Esq. (Directory Information | Send a Message)

Description

An analytical method of determining  stereoisomeric excess and/or concentration and/or absolute configuration of chiral compounds in a sample of chiral analytes that can exist in stereoisomeric (enantiomeric or diasteromeric) forms using stereodynamic ligand and metal complexes.

Applications

• Evaluate high-throughput reactions whose desired product is chiral;
• Determine the stereoisomeric excess of the desired product, thus indicating the stereoselectivity of the reaction
• Determine the concentration of the total product and/or the desired isomer, thus indicating the overall or individual yield of the reaction
• High-throughput screening of chiral compounds to sense enantiomer presence, concentration and configuration Optimization of reaction parameters, allowing the development, amplification and modification of asymmetric catalysts for instance
• Enantiopurity assessment of compound samples.

Advantages

• Provides for fast concentration and stereoisomeric excess
• High-throughput method accelerates the discovery progress
• Inexpensive way of sensing chirality in a large variety of chiral compounds
• Minimizes waste production

Background

Entantioselective synthesis and analysis is central to drug development and material science in addition to
other burgeoning areas of research. The importance of chiral compounds in the pharmaceutical industry in
particular has fueled the development of asymmetric catalysts and reaction strategies. Current optimization
methods however do not efficiently probe the concentration and enantiomeric composition of chiral
compound samples to maximize reaction potential.

In the present invention Georgetown University researchers have used highly modular, chirally flexible ligands known as “tropos ligands” as circular dichromism probes for fast concentration/configuration analysis of chiral samples, in doing so they avoid the time consuming derivatization and purification steps required in conventional analysis. When a chiral analyte potentially contained in a sample, comes into contact with the stereodynamic ligand, a stereodynamic complex is formed. The analyte coordinates with the metal center of the probe and initiates a chiral induction process that results in a spectroscopic signal change. The chiral information contained in the analyte stabilizes a distinct conformation or configuration of the stereodynamic metal complex, which can be correlated to the analyte’s stereoisomeric excess, and a change in the spectroscopic signal can be correlated to the analyte concentration.

Stage of Development

Reduced to practice

Inventors

Christian Wolf
Peng Zhang
Keith Bentley
Burcin Irfanoglu

Patent Status

Published U.S. Patent No. 10,900,941