HPLC enantioseparation of beta2-homoamino acids using crown ether-based chiral stationary phase. 2009

Róbert Berkecz, and István Ilisz, and Aleksandra Misicka, and Dagmara Tymecka, and Ferenc Fülöp, and Hee Jung Choi, and Myung Ho Hyun, and Antal Péter
Department of Inorganic and Analytical Chemistry, University of Szeged, Szeged, Hungary.

RP high-performance liquid chromatographic methods were developed for the enantioseparation of eleven unusual beta(2)-homoamino acids. The underivatized analytes were separated on a chiral stationary phase containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selector. The effects of organic (alcoholic) and acidic modifiers, the mobile phase composition and temperature on the separation were investigated. The structures of the substituents in the alpha-position of the analytes substantially influenced the retention and resolution. The elution sequence was determined in some cases: the S enantiomers eluted before the R enantiomers.

UI MeSH Term Description Entries
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D000596 Amino Acids Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins. Amino Acid,Acid, Amino,Acids, Amino
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D043844 Crown Ethers Macrocyclic polyethers with the repeating unit of (-CH2-CH2-O)n where n is greater than 2 and some oxygens may be replaced by nitrogen, sulfur or phosphorus. These compounds are useful for coordinating CATIONS. The nomenclature uses a prefix to indicate the size of the ring and a suffix for the number of heteroatoms. Aza-Oxa Crown Ethers,Crown Ether,Cryptands,Cryptate,Cryptates,Oxa-Thia Crown Ethers,Aza Oxa Crown Ethers,Crown Ethers, Aza-Oxa,Crown Ethers, Oxa-Thia,Ether, Crown,Ethers, Aza-Oxa Crown,Ethers, Crown,Ethers, Oxa-Thia Crown,Oxa Thia Crown Ethers

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