Chiral recognition and enantiomeric resolution based on host-guest complexation with crown ethers in capillary zone electrophoresis

Kuhn, Reinhard; Erni, F.; Bereuter, Thomas; Häusler, Johannes

doi:10.1021/ac00046a026

Cited by 282 publications

(123 citation statements)

References 11 publications

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“…The only one chiral crown ether used up to now in CE is 18-crown-6-tetracarboxylic acid (18C6H4), introduced by Kuhn et al [386] for the chiral separation of amino acids.…”

Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

223

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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“…The only one chiral crown ether used up to now in CE is 18-crown-6-tetracarboxylic acid (18C6H4), introduced by Kuhn et al [386] for the chiral separation of amino acids.…”

Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

223

135

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“…For these, it is necessary to add a chiral selector into the running electrolyte. Native CDs [1][2][3][4], derivatized CDs [5][6][7][8][9], crown ethers [10,11], and bile salts [12] are widely used as chiral selectors but CDs are preferred since they resolve a variety of drug substances. Furthermore, CDs are commercially available, UV transparent at short wave length usually used to monitor the enantiomers, cheap, and not toxic.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of baclofen with highly sulfated β‐cyclodextrin by capillary electrophoresis with laser‐induced fluorescence detection

Kavran-Belin

Rudaz

Veuthey

2005

J of Separation Science

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Enantioseparation of baclofen with highly sulfated b-cyclodextrin by capillary electrophoresis with laser-induced fluorescence detectionThe enantioseparation of baclofen (4-amino-3-p-chlorophenylbutyric acid) was achieved by CE-LIF with highly sulfated b-CD (HS-b-CD) as chiral selector. Naphthalene-2,3-dicarboxaldehyde was used for the derivatization of nonfluorescent baclofen. HS-b-CD (2%) containing 50 mM borate buffer at pH 9.5 was chosen as the optimal running electrolyte and applied to the analysis of baclofen enantiomers in human plasma. The linearity of calibration curves (R 2 F 0.998) for R-( -) and S-(+)-baclofen was in the 0.1-2.0 lM concentration range. After a simple ACN-protein precipitation, the LOD of baclofen in plasma sample was found as low as 50 nM.

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“…[1][2][3][4][5][6][7] The host-guest complexation mechanisms for the chiral recognition of crown ethers toward chiral amines have been well established. 2,6 The accurate chiral discrimination of each separated analyte has become an important task for their optical purity control and stereoselective pharmacokinetic studies in chiral drug development. The migration order of separated enantiomers is mainly determined by co-electrophoresis with enantiomerically pure standards and matching its migration time or relative migration time (RMT) with that of the reference.…”

mentioning

confidence: 99%

Chiral Discrimination of Aromatic Amino Acids by Capillary Electrophoresis in (+)- and (-)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid Selector Modes

2003

Bulletin of the Korean Chemical Society

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Optically active (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid (18C6H 4 ) ( Figure 1) has been successfully employed as a chiral selector in enantioseparations of diverse amino acids and chiral primary amines in capillary electrophoresis (CE). 1-7The host-guest complexation mechanisms for the chiral recognition of crown ethers toward chiral amines have been well established. 2,6 The accurate chiral discrimination of each separated analyte has become an important task for their optical purity control and stereoselective pharmacokinetic studies in chiral drug development. The migration order of separated enantiomers is mainly determined by co-electrophoresis with enantiomerically pure standards and matching its migration time or relative migration time (RMT) with that of the reference. However, crosschecking two RMT sets measured with two chiral selectors of different enantioselectivities could enhance confidence in the identification of CE peaks and the chiral discrimination as well. Based on this concept, simultaneous chiral discrimination of 15 racemic aromatic amino acids was achieved with chiral CE in neutral and charged cyclodextrin modes in our previous report. 8 The surest way of the accurate chiral discrimination is the reversal of enantiomer migration order (EMO).9-16 It is especially desirable when peak tailing, fronting or overlapping is observed. Among the diverse ways of EMO reversal developed, suppressing or reversing the direction of electroosmotic flow has been most widely used. 9,[12][13][14][15][16] In our recent report, simultaneous EMO reversal of nine chiral profens was achieved in the normal polarity and reversed polarity modes. 16 The most certain and easy method of EMO reversal might be, however, the use of two chiral selectors with the opposite chiral recognition ability, like (+)-18C6H 4 and (−)-18C6H 4 when employing crown ether-modified CE systems. However, no attempt to exploit the crosschecking each EMO measured in these two selector modes has been made in chiral CE of amino acids to date. The present study was undertaken to investigate EMO reversal by crown ether modified-CE system in the two selector modes with (+)-18C6H 4 and (−)-18C6H 4 for the chiral discrimination of nine aromatic amino acids. When (+)-18C6H 4 was added at 5 mM to 20 mM Triscitric acid buffer (pH 2.50), each enantiomeric pairs of nine aromatic amino acids studied were baseline-resolved with similar enantioselectivity and resolution factor except for 3-hydroxyphenylglycine (Table 1). 3-Hydroxyphenylglycine showed much stronger interaction with the selector than other analytes, thereby yielding a very large separation factor (1.684) and resolution factor (21.99). In good agreement with the previous reports, 1,2,4 each D-enantiomer migrated slower than the corresponding L-isomer, indicating that the D-isomers were bound more strongly with (+)-18C6H 4 in CE. The (R)-baclofen migrated ahead of the (S)-enantiomer. When (+)-18C6H 4 was replaced in the same buffer condition with its antipode, (−)-18C6H 4 (Figure 1), ...

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Chiral recognition and enantiomeric resolution based on host-guest complexation with crown ethers in capillary zone electrophoresis

Cited by 282 publications

References 11 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Enantioseparation of baclofen with highly sulfated β‐cyclodextrin by capillary electrophoresis with laser‐induced fluorescence detection

Chiral Discrimination of Aromatic Amino Acids by Capillary Electrophoresis in (+)- and (-)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid Selector Modes

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