Separation of the optical isomers of amino acids by ligand-exchange chromatography using chemically bonded chiral phases

Gübitz, Gerald; Jellenz, W.; Santi, W.

doi:10.1016/s0021-9673(00)80308-8

Cited by 145 publications

(40 citation statements)

References 21 publications

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“…Ligand-exchange chromatography (LEC) introduced by Davankov and Rogozhim [228] [229][230][231][232], a-alkyl and N-alkyl amino acids [232,233], amino acid derivatives [232], dipeptides [232], hydroxy acids [234] and thyroid hormones [235]. Subsequently, a large number of chiral LEC phases and their applications have been published [236][237][238].…”

Section: Chiral Imprinted Polymersmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Chiral Imprinted Polymersmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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“…Furthermore, chiral HPLC analyses using a column containing covalently bound (S)-proline to the stationary phase through a 3-glycidoxypropyltrimethoxysilane linkage 35 showed that (+)-2-Py-AMPA was the late eluting of the 2-Py-AMPAenantiomers (data not shown). On this type of ligand exchange column, the (R)-enantiomers of ␣-amino acids generally elute before (S)-enantiomers, 35 again suggesting that the (+)-enantiomer has the (S)-configuration.…”

Section: Configurational Assignmentmentioning

confidence: 99%

AMPA receptor agonists: Resolution, configurational assignment, and pharmacology of (+)-(S)- and (-)-(R)-2-amino-3-[3-hydroxy-5-(2-pyridyl)-isoxazol-4-yl]-propionic acid (2-Py-AMPA)

Johansen¹,

Ebert²,

Falch³

et al. 1997

Chirality

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“…The complex whose ligand is exchanged must be optically active to bring about resolution between enantiomers. The optically active species used were either covalently bound to the solid phase (e.g., Gubitz et al, 1981) or added to the mobile phase (e.g., Hare and Gil-Av, 1979) in the chromatographic run. Kurganov and Davankov (1981) and Grushka et al (1983), among others, proposed that sorbed complexes are responsible for the resolution in both the silica and the reversed phase systems, even when the chiral species are applied in the mobile phase.…”

Section: Introductionmentioning

confidence: 99%

Optically Selective Adsorption of α-Amino Acids on Montmorillonite-Cu-1-Lysine Complexes in High-Pressure Liquid Chromatography

Tsvetkov

Mingelgrin

1987

Clays and clay miner.

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Abstract--Optically active cationic complexes adsorbed on montmorillonite can be used for the resolution ofracemic mixtures. Montmorillonite-Cu-lysine systems were used as a solid phase in high-pressure liquid chromatography for the resolution of the optical isomers of a-amino acids. Selectivity constants > 1.5 were measured for phenylalanine and tryptophan. The selectivity constants for the amino acids containing saturated-hydrocarbon side chains were in the range of 1.25-1.44. The montmorillonite-Cu-l-lysine complex displayed a stronger affinity for the 1-isomers of a-amino acids than for the d-isomers at pHs near neutrality. Inasmuch as surface-catalyzed peptide formation on clays has been proposed as a step in chemical evolution, this stronger affinity between the clay-Cu-l-amino acid complex and 1-amino acids might have been significant in prebiotic evolution. The mechanism of optical resolution probably involved ligand exchange. Optimizing the choice of the optically active ligands and of the chelating cation in the chiral agent may improve the resolution of the optical isomers.

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Separation of the optical isomers of amino acids by ligand-exchange chromatography using chemically bonded chiral phases

Cited by 145 publications

References 21 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

AMPA receptor agonists: Resolution, configurational assignment, and pharmacology of (+)-(S)- and (-)-(R)-2-amino-3-[3-hydroxy-5-(2-pyridyl)-isoxazol-4-yl]-propionic acid (2-Py-AMPA)

Optically Selective Adsorption of α-Amino Acids on Montmorillonite-Cu-1-Lysine Complexes in High-Pressure Liquid Chromatography

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