High-performance liquid chromatographic enantioseparation of beta-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase.
Direct reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of 14 unnatural beta-amino acids, including several beta-3-homo-amino acids on a chiral stationary phase containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid bonded to 3-aminopropyl silica gel as chiral selector. The effects of the organic and the acidic modifiers and the mobile phase composition on the separation were investigated. The natures and positions of the substituents on the aromatic ring substantially influenced the retention and enantioseparation. The elution sequence in most cases was determined and the R enantiomers were eluteted before the S enantiomers.
Berkecz
Róbert
R
Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.
Sztojkov-Ivanov
Anita
A
Ilisz
István
I
Forró
Eniko
E
Fülöp
Ferenc
F
Hyun
Myung Ho
MH
Péter
Antal
A
D000596:Amino Acids / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification*; D002264:Carboxylic Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D043844:Crown Ethers / Q000737:chemistry*; D015394:Molecular Structure; D015203:Reproducibility of Results; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D002264:Carboxylic Acids; D043844:Crown Ethers; C090732:18-crown-6 2,3,11,12-tetracarboxylic acid; D012822:Silicon Dioxide