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The role of pi-acidic and pi-basic chiral stationary phases in the high-performance liquid chromatographic enantioseparation of unusual beta-amino acids
Authors:Ilisz István  Berkecz Róbert  Forró Eniko  Fülöp Ferenc  Armstrong Daniel W  Péter Antal
Institution:Department of Inorganic and Analytical Chemistry, University of Szeged, Szeged, Hungary.
Abstract:The application of 3,5-dimethylphenyl-carbamoylated-beta-cyclodextrin (Cyclobond I 2000 DMP) and 2,6-dinitro-4-trifluoromethylphenyl-ether-beta-cyclodextrin-based (Cyclobond DNP) chiral stationary phases for the high-performance liquid chromatographic enantioseparation of unusual beta-amino acids is reported. The investigated amino acids were saturated or unsaturated alicyclic beta-3-homo-amino acids and bicyclic beta-amino acids. Prior to chromatographic analyses, all amino acids were transformed to N-3,5-dinitrobenzoyl- or N-3,5-dimethylbenzoyl form to ensure a pi-acidic or pi-basic function and to enhance the pi-acidic-pi-basic interactions between analytes and chiral selectors. Chromatographic results are given as retention, separation and resolution factors. The chromatographic conditions were varied to achieve optimal separation. The sequence of elution of the enantiomers was determined in some cases.
Keywords:high‐performance liquid chromatography (HPLC)  chiral stationary phases (CSPs)  3  5‐dimethylphenyl‐carbamoylated‐β‐cyclodextrin‐based column (Cyclobond I 2000 DMP)  2  6‐dinitro‐4‐trifluoromethylphenyl‐ether‐β‐cyclodextrin‐based column (Cyclobond DNP)  unusual β‐3‐homo amino acids  bicyclic‐β‐amino acids
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