Chiral separation of neutral species by capillary electrophoresis evaluation of a theoretical model

Surapaneni, Sekhar; Ruterbories, Kenneth J.; Lindstrom, Terry D.

doi:10.1016/s0021-9673(96)00874-6

Cited by 44 publications

(27 citation statements)

References 23 publications

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“…A theoretical model for the optimization of chiral separations by CE of neutral species, when a combination of neutral and ionizable CDs are used, was developed by Surapaneni et al [344]. This model was tested experimentally for the separation of the enantiomers of LY213829 and its four isomeric sulfoxide metabolites by using SBE-p-CD in conjunction with native p-CD or the neutral p-CD derivatives HP-P-CD and TM-P-CD.…”

Section: Buffer Systems Containing More Than One Chiralmentioning

confidence: 99%

Separation of chiral compounds by capillary electrophoresis

1998

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This review presents the different chiral selectors used in capillary electrophoresis (CE) for the separation of enantiomers. The use of charged cyclodextrins, crown ethers, polysaccharides, proteins, natural and synthetic micelles, macrocyclic antibiotics and ergot alkaloids is discussed in detail. Neutral native and derivatized cyclodextrins are not treated because several review articles have already been published on this topic. Recent developments like the application of two chiral selectors in the same background electrolyte are highlighted.

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Section: Buffer Systems Containing More Than One Chiralmentioning

confidence: 99%

Separation of chiral compounds by capillary electrophoresis

1998

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“…The electrophoretic migration of the enantiomeric compounds can be modified through the complexation of the enantiomers of analytes with various CDs, thus resulting in differences in the binding constants and/or the mobility of the enantiomeric complexes. For neutral chiral compounds, enantioseparation can be achieved with charged CDs [3,[8][9][10][11][12][13][14][15][16][17] or with dual CD systems consisting of a charged CD and a neutral CD [15][16][17][18][19][20][21][22][23][24][25][26] or two charged CDs [27]. Enantioseparation of neutral analytes is not achievable with neutral CDs alone, unless the electrophoretic system is a CDcontaining buffer system which can form charged complexes with the analyte enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparations of hydrobenzoin and structurally related compounds in capillary zone electrophoresis using heptakis(2,3‐dihydroxy‐6‐O‐sulfo)‐β‐cyclodextrin as chiral selector and enantiomer migration reversal of hydrobenzoin with a dual cyclodextrin system in the presence of borate complexation

Lin

Fang

et al. 2004

Electrophoresis

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We investigated the enantioseparations of racemic hydrobenzoin, together with benzoin and benzoin methyl ether, in capillary electrophoresis (CE) using the single-isomer heptakis(2,3-dihydroxy-6-O-sulfo)-beta-cyclodextrin (SI-S-beta-CD) as a chiral selector in the presence and absence of borate complexation and enantiomer migration reversal of hydrobenzoin with a dual CD system consisting of SI-S-beta-CD and beta-CD in the presence of borate complexation at pH 9.0 in a borate buffer. The enantioselectivity of hydrobenzoin increased remarkably with increasing SI-S-beta-CD concentration and the enantioseparation depended on CD complexation between hydrobenzoin-borate and SI-S-beta-CD. The (S,S)-enantiomer of hydrobenzoin-borate complexes interacted more strongly than the (R,R)-enantiomer with SI-S-beta-CD. The enantiomers of hydrobenzoin could be baseline-resolved in the presence of SI-S-beta-CD at a concentration as low as 0.1% w/v, whereas the three test analytes were simultaneously enantioseparated with addition of 0.3% w/v SI-S-beta-CD or at concentrations >2.0% w/v in a borate buffer and 0.5% w/v in a phosphate background electrolyte at pH 9.0. Compared with the results obtained previously using randomly sulfated beta-CD (MI-S-beta-CD) in a borate buffer, enantioseparation of these three benzoin compounds is more advantageously aided by SI-S-beta-CD as the chiral selector. The enantioselectivity of hydrobenzoin depended greatly on the degree of substitution of sulfated beta-CD. Moreover, binding constants of the enantiomers of benzoin compounds to SI-S-beta-CD and those of hydrobenzoin-borate complexes to SI-S-beta-CD were evaluated for a better understanding of the role of CD complexation in the enantioseparation and chiral recognition. Enantiomer migration reversal of hydrobenzoin could be observed by varying the concentration of beta-CD, while keeping SI-S-beta-CD at a relatively low concentration. SI-S-beta-CD and beta-CD showed the same chiral recognition pattern but they exhibited opposite effects on the mobility of the enantiomers.

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“…Gareil et al [194], Surapaneni et al [195], Crommen and co-workers [196,197], and Desbene et al [198] have proposed mathematical models optimizing dual chiral separation systems. All of these models allow in principle a more or less complete description of the separation system if one suggests that the boundary conditions are correctly selected.…”

Section: Mathematical Models Of Ekc Enantioseparationsmentioning

confidence: 99%

Chiral Recognition and Enantioseparation Mechanisms in Capillary Electrokinetic Chromatography

Chankvetadze

2010

Chiral Recognition in Separation Methods

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Chiral separation of neutral species by capillary electrophoresis evaluation of a theoretical model

Cited by 44 publications

References 23 publications

Separation of chiral compounds by capillary electrophoresis

Separation of chiral compounds by capillary electrophoresis

Chiral Recognition and Enantioseparation Mechanisms in Capillary Electrokinetic Chromatography

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