Chemically bonded chiral stationary phases for the separation of racemates by high performance liquid chromatography

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

doi:10.1002/jhrc.1240020308

Cited by 72 publications

(6 citation statements)

References 10 publications

(2 reference statements)

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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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“…Davankov et al (1980Davankov et al ( , 1981 modified commercial HPLC columns by grafting alkyl derivatives of a-amino acids such as n-decyl-L-histidine or n-hexa decyl-Lproline onto the resin for enantiomeric resolution. Gübitz et al (1979Gübitz et al ( , 1981Gübitz et al ( , 1982 adapted this principle to HPLC using silica gel phases to which amino acid(s) were chemically bonded. Since then several papers dealing with different applications of chiral Ligand Exchange Chromatography (LEC) have appeared wherein Cu(II) complexes of optically pure a-amino acids and their derivatives have been applied as CSPs, usually after binding covalently or hydrophobically to solid column support (Davankov, 1988(Davankov, , 1994(Davankov, , 2000(Davankov, , 2003Kurganov, 2001).…”

Section: Amino Acids and Their Derivatives As Ligands For Enantiosepamentioning

confidence: 99%

“…Gübitz et al . (, , ) adapted this principle to HPLC using silica gel phases to which amino acid(s) were chemically bonded. Since then several papers dealing with different applications of chiral Ligand Exchange Chromatography (LEC) have appeared wherein Cu(II) complexes of optically pure α ‐amino acids and their derivatives have been applied as CSPs, usually after binding covalently or hydrophobically to solid column support (Davankov, , , , ; Kurganov, ).…”

Section: Direct Resolution Using Amino Acids As Chiral Impregnating Rmentioning

confidence: 99%

Amino acids as chiral selectors in enantioresolution by liquid chromatography

Bhushan

Dixit

2012

Biomedical Chromatography

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Amino acids are unique in terms of their structural features and multidimensional uses. With their simple structures and the ready availability of both enantiomers, amino acids not only serve as a chiral pool for synthesis but also provide an inexpensive pool for resolution studies. There has been no attempt to review the application of amino acids as chiral selectors for chromatographic enantioresolution of pharmaceuticals and other compounds. The present paper deals with application of l-amino acids and complexes of l-amino acids with a metal ion, particularly Cu(II), as an impregnating reagent in thin-layer chromatography or as a chiral ligand exchange reagent or a chiral mobile phase additive in both thin-layer chromatography and high-performance liquid chromatography. Enantiomeric resolution of β-blockers, nonsteroidal anti-inflammatories, amino acids (and their derivatives) and certain other compounds is discussed.

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“…Gübitz et al . transferred this technique to HPLC by preparing chemically bonded phases on silica basis 9, 10. Amino acids were immobilised via 3‐glycidoxypropyltrimethoxysilane as a spacer to silica gel, and copper(II) was used as complex‐forming agent.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of amino acids, α‐hydroxy acids, and dipeptides by ligand‐exchange CEC using silica‐based chiral stationary phases

et al. 2009

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This work deals with the application of silica-based ligand-exchange chiral stationary phases (CSPs) for the enantioseparation of underivatized amino acids, alpha-hydroxy acids, and dipeptides with packed CEC. Two different possibilities of preparing silica-based CSPs are presented. One phase contains L-4-hydroxyproline chemically bonded via a spacer to 3 mum silica material. The other approach makes use of N-decyl-L-4-hydroxyproline dynamically coated on a reversed-phase packed capillary. Dynamical coating of reversed-phase material represents a simple alternative to prepare CSP. A comparison of the chemically bonded phase with the dynamically coated CSP by means of resolution of complex-forming analytes is presented. The chemically bonded phase was found to be superior to the dynamically coated phase in terms of resolution of amino acids and dipeptides. However, the dynamically coated CSP was found to be especially suitable for the separation of alpha-hydroxy acids. Both techniques are applicable for enantiomer purity tests.

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Chemically bonded chiral stationary phases for the separation of racemates by high performance liquid chromatography

Cited by 72 publications

References 10 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Amino acids as chiral selectors in enantioresolution by liquid chromatography

Enantioseparation of amino acids, α‐hydroxy acids, and dipeptides by ligand‐exchange CEC using silica‐based chiral stationary phases

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