Enantioselective HPLC of potentially CNS-active acidic amino acids with a Cinchona carbamate based chiral stationary phase.
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.
Sardella
Roccaldo
R
Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, 06123 Perugia, Italy.
Lämmerhofer
Michael
M
Natalini
Benedetto
B
Lindner
Wolfgang
W
D024342:Amino Acids, Acidic / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D002219:Carbamates / Q000737:chemistry; D002491:Central Nervous System Agents / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002930:Cinchona Alkaloids / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D013237:Stereoisomerism
D024342:Amino Acids, Acidic; D002219:Carbamates; D002491:Central Nervous System Agents; D002930:Cinchona Alkaloids