Enantioselective HPLC of potentially CNS-active acidic amino acids with a Cinchona carbamate based chiral stationary phase

Chirality. 2008 Mar;20(3-4):571-6. doi: 10.1002/chir.20529.

Abstract

A tert-butylcarbamoylquinine-based chiral stationary phase (Chiralpak QN-AX) has been employed for the enantiomer separation of underivatized chiral acidic amino acids, viz. 4-carboxyphenylalanine (4-CPHE), 1-aminoindan-1,5-dicarboxylic acid (AIDA), 2-(5-carboxy-3-methyl-2-thienyl)glycine (3-MATIDA), 2-(4-carboxy-5-methyl-2-thienyl)glycine (5-MATIDA), and 2-(2'-carboxy-3'-phenylcyclopropyl)glycine (PCCG). Some of the acidic amino acids have potential activity on the central nervous system and are thus of great interest. A stereoselective HPLC method that allows the baseline resolution of all the five test solutes has been developed. For that purpose the mobile phase composition (pH, organic modifier, and type) and flow rate were optimized. The final method makes use of mild elution conditions, namely methanol - 0.8 M ammonium acetate buffer (97.5:2.5; v/v) pH 5.5 which are also compatible with mass spectrometric detection.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids, Acidic / chemistry*
  • Amino Acids, Acidic / isolation & purification*
  • Amino Acids, Acidic / pharmacology
  • Carbamates / chemistry
  • Central Nervous System Agents / chemistry*
  • Central Nervous System Agents / isolation & purification*
  • Central Nervous System Agents / pharmacology
  • Chromatography, High Pressure Liquid / methods*
  • Cinchona Alkaloids / chemistry
  • Hydrogen-Ion Concentration
  • Stereoisomerism

Substances

  • Amino Acids, Acidic
  • Carbamates
  • Central Nervous System Agents
  • Cinchona Alkaloids