Chiral separations by host-guest complexation with cyclodextrin and crown ether in capillary zone electrophoresis

Kuhn, Reinhard; Stoecklin, F.; Erni, F.

doi:10.1007/bf02276847

Cited by 263 publications

(110 citation statements)

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“…The uncomplexed positively charged analyte moves toward the cathodic end (detector end) by its own native electrophoretic velocity. The greater the interaction with the CD the longer the migration time of the analyte [21]. M␤CD, heptakis-di-o-methyl, and tri-o-methyl-␤-CD were studied over the concentration range of 10 -80 mM.…”

Section: Resultsmentioning

confidence: 99%

“…Since pH 2 was used, which is low enough to suppress the electroosmotic flow by not allowing enough deprotonation or ionization of the silinol groups that form the internal surface of the capillary, the V eo term equals zero [21,23,24]. This condition was proven by using a neutral marker that was not observed by the UV detector following 5 h of analysis time.…”

Section: Calculation Of the Local Anesthetic-cd Interaction By Ce Andmentioning

confidence: 99%

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Comparison of local anesthetic-cyclodextrin non-covalent complexes using capillary electrophoresis and electrospray ionization mass spectrometry

Alnouti

Bartlett

2002

J. Am. Soc. Mass Spectrom.

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Non-covalent complexes between three derivitized cyclodextrins (CD's) and six local anesthetics were studied using capillary electrophoresis (CE) and electrospray ionization mass spectrometry (ESI-MS). The CE study was performed using the complete filling technique (CFT). A comparison between the migration data from CE and ESI-MS inclusion complex peak abundances was made representing the association between local anesthetics and CD's in the solution and the gas phase, respectively. The results from this study showed comparable behavior of the complexes in the CE and mass spectrometer, indicating similarity in the parameters controlling the stability of these complexes. Therefore, the formation of specific non-covalent complexes, as shown in this study, could be used to predict the behavior of a complexing agent with a substrate in the solution phase by observing data obtained from ESI-MS. (J Am Soc Mass Spectrom 2002, 13, 928 -935)

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Section: Resultsmentioning

confidence: 99%

Section: Calculation Of the Local Anesthetic-cd Interaction By Ce Andmentioning

confidence: 99%

Comparison of local anesthetic-cyclodextrin non-covalent complexes using capillary electrophoresis and electrospray ionization mass spectrometry

Alnouti

Bartlett

2002

J. Am. Soc. Mass Spectrom.

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“…Kuhn et al [39] used chiral crown ether 18C 6 H 4 in CE and explain the chiral recognition mechanisms and as per authors host-guest complexes of enantiomers are formed which are stabilized by hydrogen bonding, electrostatic interactions and steric affects. The carboxylic groups of crown ether; perpendicular to the plane of the ring; form a chiral barrier which divides the space available for the substituents at the chiral centre of the enantiomers into two domains.…”

Section: Mechanisms Of Chiral Resolutionmentioning

confidence: 99%

Chiral Analyses of Pollutants by Capillary Electrophoresis

Ali¹

2010

TOCBMJ

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Abstract:The determination of enantiomeric composition of chiral xenobiotics and pollutants is a very difficult job due to their low amounts and poor detection by commonly used UV detector. But this sort of analysis is an important issue from the health point of view. The chiral analyses of these notorious pollutants by capillary electrophoresis have been discussed in this article. This review discusses the new trends and advancements, which have been achieved in the analyses of chiral pollutants using capillary electrophoresis and the state-of-art of their enaniomeric resolution. This article focuses on sample treatment, applications, optimization, detection, mechanisms of chiral resolution and future perspectives of CE in chiral resolution of xenobiotics. Besides, efforts have also been made to suggest the improvement in CE machine to make it ideal for the analyses of chiral xenobiotics at trace levels.

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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.…”

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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 separations by host-guest complexation with cyclodextrin and crown ether in capillary zone electrophoresis

Cited by 263 publications

References 28 publications

Comparison of local anesthetic-cyclodextrin non-covalent complexes using capillary electrophoresis and electrospray ionization mass spectrometry

Comparison of local anesthetic-cyclodextrin non-covalent complexes using capillary electrophoresis and electrospray ionization mass spectrometry

Chiral Analyses of Pollutants by Capillary Electrophoresis

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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