Details

Project TitleChiral 1,8-Diarylnaphthalenes, Methods of Making Them, and Their Use as Sensors
Track Code2003-005
Short Description

Novel fluorescent molecular sensors can be used rapidly measure the enantiomeric excess of chiral chemical compounds without the need for time consuming chromatography techniques. Many biologically active compounds (flavors, nutrients, agrochemicals, pharmaceutical drugs) are chiral and used in enantiopure form. For example, while one enantiomer of a chiral drug can exhibit the desired pharmacological activity the other enantiomer can be toxic, so accurate measurements of enantio-purity are critical. These sensors utilize fluorescence and UV spectroscopy to allow the quantitative measurement of enantiopurity in chiral molecules. These sensors can be used for high-throughput synthetic screening (HTS) to rapidly detect the enantioselectivity of chemical reaction products and to determine a compound’s stability to racemization under different conditions.

AbstractNone
 
TagsCalvert Research Institute, chemistry, Clean-up Tool, method, otc website
 
Posted DateSep 4, 2014 5:23 PM

Manager

Name
Thomas Houze

Applications

  • High-throughput screening of asymmetric reactions
  • Differentiating between and detecting/quantifying enantiopurity of a broad range of chiral compounds including carboxylic acids, alcohols, amines, and amides

Advantages

  • An alternative to time consuming chromotagraphic analysis
  • Ability to rapidly detect the enantioselectivity of in HTS of asymmetric reactions
  • In situ detection allows for the screening of a compound’s stability to racemization.

Relevant Publications

"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.

Stage of Development

Proof of principle and different applications of the technology have been successfully demonstrated with a variety of chiral substrates.

Patent Status

US Patent Application entitled, “Chiral 1,8-Diarylnaphthalenes, Methods of Making Them, and Their Use as Sensors” published under US/ 20070276140 on November 26, 2007.

Relevant Publications

Patent Status