Ligand-exchange chromatography

Davankov, V. A.; Semechkin, A.V.

doi:10.1016/s0021-9673(00)93538-6

Cited by 195 publications

(66 citation statements)

References 144 publications

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“…LEC has been found to be notably effective for the separation of free or derivatized common as well as special and non-protein DLamino acids (DL-AAs) [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. In particular Davankov and his coworkers initiated and stimulated much work on LEC and regularly have reviewed the progress in this field of separation science [1,4,[18][19][20][21]. Bonded and free L-His show good chiral discrimination in LEC as a result of the participation of a nitrogen atom in the imidazol ring [9,10].…”

Section: Introductionmentioning

confidence: 99%

Ligand-exchange chromatographic separation of DL-amino acids on aminopropylsilica-bonded chirals-triazines

Wachsmann

Brückner

1998

Chromatographia

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SummaryChiral stationary phases (CSPs) were synthesized by reaction of aminopropylsilica (APS) with chiral monochloro-s-triazines (MCTs). MCTs were obtained by reaction of 2,4,6-trichloro-s-triazine (cyanuric chloride) with one equivalent of methanol and, subsequently, with one equivalent of L-proline tert butyl ester (HPro-OtBu) or N-ten butyloxycarbonyl-L-lysine tert butyl ester (Boc-Lys-OtBu). End-capping of unreacted amino groups of APS with acetic anhydride, followed by trifluoroacetolytic cleavage of the protecting groups of amino acids (AAs), afforded two chiral stationary phases bearing either L-proline (CSP-3) or L-lysine (CSP-4) as chiral selector. Using ligand-exchange chromatography with addition of Cu 2+ to the mobile phase, enantiomers of free DL-AAs and a few N-(2,4-dinitrophenyl)-DL-AAs were separated on CSP-3, whereas N-(dansyl)-DL-AAs were separated on CSP-4.

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Section: Introductionmentioning

confidence: 99%

Ligand-exchange chromatographic separation of DL-amino acids on aminopropylsilica-bonded chirals-triazines

Wachsmann

Brückner

1998

Chromatographia

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“…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.…”

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confidence: 99%

Separation of amino acid enantiomers by micelle-enhanced ultrafiltration

et al. 2000

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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.

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“…52 As a result, their range of applications is limited and only useful for the chiral resolution of enantiomers containing electron-donating atoms, such as oxygen, nitrogen, and sulfur. The reversed phase mode with aqueous buffers can be used with these columns.…”

Section: Chiral Separation With Hplcmentioning

confidence: 99%

Chloroperoxidase Catalyzed Enantioselective Epoxidation of Selected Olefins and Regiospecific Degradation of Dimethylsulfoniopropionate

Chen¹

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Ligand-exchange chromatography

Cited by 195 publications

References 144 publications

Ligand-exchange chromatographic separation of DL-amino acids on aminopropylsilica-bonded chirals-triazines

Ligand-exchange chromatographic separation of DL-amino acids on aminopropylsilica-bonded chirals-triazines

Separation of amino acid enantiomers by micelle-enhanced ultrafiltration

Chloroperoxidase Catalyzed Enantioselective Epoxidation of Selected Olefins and Regiospecific Degradation of Dimethylsulfoniopropionate

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