Sensing of enantiomeric excess in chiral carboxylic acids

Chem Commun (Camb). 2015 Apr 4;51(26):5770-3. doi: 10.1039/c5cc00376h.

Abstract

Cinchona alkaloids (quinine, quinidine, cinchonine, cinchonidine) alkylated at N(1) with chloromethyl anthracene can serve as fluorescent sensors for chiral carboxylic acids. These cinchona ammonium salts are shown to bind chiral carboxylic acids while displaying an increase in fluorescence intensity that can be utilized in determination of enantiomeric excess (ee). Sensor arrays composed of four cinchona ammonium salts are used for quantitative analysis of ee in several non-steroidal anti-inflammatory drugs (NSAIDs), such as enantiomers of ibuprofen, ketoprofen, and naproxen.

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / analysis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Carboxylic Acids / analysis*
  • Carboxylic Acids / chemistry*
  • Crystallography, X-Ray
  • Fluorescence
  • Fluorescent Dyes / analysis
  • Fluorescent Dyes / chemistry
  • Ibuprofen / analysis*
  • Ibuprofen / chemistry
  • Ketoprofen / analysis*
  • Ketoprofen / chemistry
  • Models, Molecular
  • Molecular Structure
  • Naproxen / analysis*
  • Naproxen / chemistry
  • Stereoisomerism

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Carboxylic Acids
  • Fluorescent Dyes
  • Naproxen
  • Ketoprofen
  • Ibuprofen