Stereoselective Sensors for Amino Acids, Amines, Amine Alcohols and Carboxylic Acids: Chiral 1,8-Diarylnaphthalenes, Methods of Production and Use
Section: For Industry
Category(ies): Chemistry
Reference #: WOCH222001
OTC Contact: Dave Odelson, Ph.D. (Directory Information | Send a Message)
Description
Most biologically active compounds (flavors, nutrients, agrochemicals, pharmaceutical drugs) are chiral and used in enantiopure form. In order to test and market safe food additives, cosmetics and drugs one has to verify the enantiomeric composition of the active ingredient because enantiomers can have dramatically different effects: while one enantiomer of a chiral drug can exhibit the desired pharmacological activity the other enantiomer can be very toxic. It is therefore important to develop methods that can be used for high-throughput screening (HTS) of the stereochemical composition and stereochemical integrity, i.e. stability to racemization, of chiral compounds. The high demand for time-efficient, accurate and sensitive enantioselective analysis provides a compelling rationale for developing chiral sensors that can be used for HTS of small sample amounts. We have developed molecular C2-symmetric 1,8-diheteroarylnaphthalene-derived sensors suitable to enantioselective fluorescence and UV analysis of amino acids, amines, amino alcohols, and carboxylic acids. These sensors can also be used for copper-catalyzed C-N and C-S bond formation, supramolecular chemistry, arene-arene p-stacking, and solid-state synthesis. These sensors utilize fluorescence and UV spectroscopy to quantitatively measure chiral recognition.
Applications
Applications:- High-throughput screening of asymmetric reactions;
- Measurements of the enantiomeric composition of chiral analytes;
- Differentiating between and detecting/quantifying enantiomers of a broad range of chiral compounds including carboxylic acids, alcohols, amines, and amides;
- Asymmetric catalysis;
- Sensing of various metal ions such as alkali, alkaline, earth or transition metals;and
- Biomedical applications involving selective interactions with RNA and/or DNA targets.
- Increased sensitivity and selectivity
- Fast analysis
- Stable
- Inexpensive
- Real-time analysis
- Little waste produced High accuracy and precision
Advantages
Stage of Development
Stage of Development: Proof of principle and different applications of the technology have been successfully demonstrated.
Inventors: Christian Wolf, and Xuefeng Mei.
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.
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.
