Chiral discrimination by ligand-exchange chromatography: A comparison between phenylalaninamide-based stationary and mobile phases

Marchelli, Rosangela; Corradini, Roberto; Bertuzzi, Terenzio; Galaverna, Gianni; Dossena, Arnaldo; Gasparrini, Francesco; Galli, Beatrice; Villani, Claudio; Misiti, D.

doi:10.1002/(sici)1520-636x(1996)8:6<452::aid-chir7>3.0.co;2-e

Cited by 27 publications

(17 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Subsequently, a large number of chiral LEC phases and their applications have been published [236][237][238]. Recent developments are the preparation of a chiral stationary phase by covalent attachment of S-and R-phenylalaninamide [239] and (S,R)-and (S, S) -N 2 -(2-hydroxypropyl)-phenylalaninamide [240] to silica. G . u ubitz et al [241] prepared two new chiral ligand-exchange chromatography (CLEC-) phases by binding l-proline via a (2-hydroxycyclohexyl)ethylene and a 6-hydroxy-4-oxa-8-aza-n-decene spacer to silica.…”

Section: Chiral Imprinted Polymersmentioning

confidence: 99%

“…Numerous publications deal with the application of this basic technique using different metal complexes [236][237][238]. Selected examples of recent developments in this field are the use of (S)-phenylalaninamide [239], (S,S)-N 2 -(2-hydroxypropyl)-phenylalaninamide [240] and (S,S)-N,N'-bis(phenylalanyl)ethanediamine as chiral additives to the mobile phase.…”

Section: Chiral Imprinted Polymersmentioning

confidence: 99%

See 1 more Smart Citation

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

View full text Add to dashboard Cite

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.

show abstract

Section: Chiral Imprinted Polymersmentioning

confidence: 99%

Section: Chiral Imprinted Polymersmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

View full text Add to dashboard Cite

show abstract

“…This separation technique is closely related to chiral ligand exchange chromatography (CLEC), in which amino acid derivatives are used as chiral selectors and are chemically bound or physically adsorbed to the stationary phase. 17 Many examples can be found in the literature that make use of amino acid derivatives and copper(II) ions in the stationary phase, [18][19][20][21][22] or in the mobile phase 23,24 to separate racemic mixtures of amino acids. However, to the best of our knowledge these separation systems were only used for analytical or small-scale preparation purposes, whereas the MEUF system can potentially be used to separate enantiomers on a large scale.…”

mentioning

confidence: 99%

Separation of amino acid enantiomers by micelle-enhanced ultrafiltration

et al. 2000

View full text Add to dashboard Cite

A Micelle-enhanced ultrafiltration (MEUF) separation process was investigated that can potentially be used for large-scale enantioseparations. Copper(II)-amino acid derivatives dissolved in nonionic surfactant micelles were used as chiral selectors for the separation of dilute racemic amino acids solutions. For the alpha-amino acids phenylalanine, phenylglycine, O-methyltyrosine, isoleucine, and leucine good separation was obtained using cholesteryl L-glutamate and Cu(II) ions as chiral selector with an operational enantioselectivity (alpha(op)) up to 14.5 for phenylglycine. From a wide set of substrates, including four beta-amino acids, it was concluded that the performance of this system is determined by two factors: the hydrophobicity of the racemic amino acid, which results in a partitioning of the racemic amino acid over micelle and aqueous solution, and the stability of the diastereomeric complex formed upon binding of the amino acid with the chiral selector. The chiral hydrophobic cholesteryl anchor of the chiral selector also plays an active role in the recognition process, since inversion of the chirality of the glutamate does not yield the reciprocal enantioselectivities. However, if the cholesteryl group is replaced by a nonchiral alkyl chain, reciprocal operational enantioselectivities are found with enantiomeric glutamate selectors.

show abstract

“…Several chromatographic [36][37][38] and electrophoretic methods [39,40] are based on using chiral stationary phases or chiral selectors as CMPA for separation of AA enantiomers.…”

Section: Methods For Direct Enantioseparationmentioning

confidence: 99%

“…CLEC model suggests that the complex undergoes specific interaction with the enantiomer (i.e., with the ligand donating a lone pair of electrons); the metal ion simultaneously coordinates the chiral selector and the enantiomer to be separated. The metal ion used in CLEC especially the Cu(II) causes large background noise and decreases the sensitivity of UV-visible detector [38]. At pH higher than 5 the precipitation of Cu is also reported and such a precipitation results in choking of chromatographic column.…”

Section: Copper (Ii) Amino Acid Complexes As Reagents In Lecmentioning

confidence: 99%