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Enantioselective HPLC of potentially CNS‐active acidic amino acids with a cinchona carbamate based chiral stationary phase
Author(s) -
Sardella Roccaldo,
Lämmerhofer Michael,
Natalini Benedetto,
Lindner Wolfgang
Publication year - 2008
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20529
Subject(s) - chemistry , enantiomer , ammonium acetate , glycine , high performance liquid chromatography , amino acid , cinchona , chiral derivatizing agent , enantioselective synthesis , chromatography , elution , stereoselectivity , methanol , resolution (logic) , chiral column chromatography , ammonium , organic chemistry , carbamate , catalysis , biochemistry , artificial intelligence , computer science
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. Chirality, 2008. © 2008 Wiley‐Liss, Inc.