Fluorescent Molecular Sensors for Measuring Chirality without Chromatography

OVERVIEW

Georgetown's innovative fluorescent molecular sensors revolutionize the measurement of enantiomeric purity in chiral chemical compounds, offering a rapid and precise alternative to time-consuming chromatography techniques. Chirality plays a pivotal role in various sectors, including pharmaceuticals, agrochemicals, flavors, and nutrients, where the accurate determination of enantiopurity is crucial for safety and efficacy. These sensors employ fluorescence and UV spectroscopy, enabling quantitative enantiopurity analysis, high-throughput synthetic screening (HTS), and stability assessments under different conditions.

BACKGROUND

Chirality is a fundamental aspect of many biologically active compounds, particularly in pharmaceuticals and agrochemicals, where the purity of single enantiomers is critical. Traditional methods for enantiomeric analysis, such as chiral chromatography, often suffer from cost, time, and sensitivity limitations. Our innovative enantioselective fluorescence sensors offer a superior alternative, with advantages including real-time analysis, cost-effectiveness, and high sensitivity. These sensors are poised to transform the field by combining well-defined stereoselective recognition with the power of fluorescence detection, providing a practical and efficient solution for enantiomeric purity determination in various industries.

Benefit

• Faster than traditional chromatographic analysis
• Rapidly detects enantioselectivity in high-throughput screening (HTS) of asymmetric reactions
• In-situ detection assesses compound stability against racemization

Market Application

• Accelerating high-throughput screening for asymmetric reactions
• Distinguishing and quantifying enantiopurity in various chiral compounds, such as carboxylic acids, alcohols, amines, and amides

Publications

• US patent No. 7,888,509
• “An enantioselective fluorescence sensing assay for quantitative analysis of chiral carboxylic acids and amino acid derivatives.” Chem Commun (Camb). 2006 Oct 28;(40):4242-4.
• “Synthesis of a sterically crowded atropisomeric 1,8-diacridylnaphthalene for dual-mode enantioselective fluorosensing.” J Org Chem. 2006 Mar 31;71(7):2854-61.
• “Enantioselective analysis of an asymmetric reaction using a chiral fluorosensor.” Org Lett. 2005 Sep 1;7(18):4045-8.
• “Synthesis and stereodynamics of highly constrained 1,8-bis(2,2′-dialkyl-4,4′-diquinolyl)naphthalenes (2).” J Org Chem. 2005 Apr 15;70(8):2930-8.
• “Enantioselective sensing of chiral carboxylic acids.” J Am Chem Soc. 2004 Nov 17;126(45):14736-7.
• “Highly congested nondistorted diheteroarylnaphthalenes: model compounds for the investigation of intramolecular pi-stacking interactions.” J Org Chem. 2005 Mar 18;70(6):2299-305
• “A highly congested N,N’-dioxide fluorosensor for enantioselective recognition of chiral hydrogen bond donors.” Chem Commun (Camb). 2004 Sep 21;(18):2078-9.