Enantiomeric separation of N-protected amino acids by non-aqueous capillary electrophoresis with dimeric forms of quinine and quinidine derivatives serving as chiral selectors

Piette, Véronique; Lindner, Wolfgang; Crommen, Jacques

doi:10.1016/s0021-9673(01)01591-6

Cited by 29 publications

(19 citation statements)

References 11 publications

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“…The main chiral selectors used in NACE for chiral separations are CDs and their derivatives (see Table 1) [56]. Ion-pairing compounds, such as camphorsulfonate enantiomers [57] and quinine derivatives, have also been employed [58][59][60][61][62].…”

Section: Nonaqueous Cementioning

confidence: 99%

Sensitive chiral analysis by capillary electrophoresis

García-Ruiz

Marina

2006

Electrophoresis

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Sensitive chiral analysis by capillary electrophoresisIn this review, an updated view of the different strategies used up to now to enhance the sensitivity of detection in chiral analysis by CE will be provided to the readers. With this aim, it will include a brief description of the fundamentals and most of the recent applications performed in sensitive chiral analysis by CE using offline and online sample treatment techniques (SPE, liquid-liquid extraction, microdialysis, etc.), on-column preconcentration techniques based on electrophoretic principles (ITP, stacking, and sweeping), and alternative detection systems (spectroscopic, spectrometric, and electrochemical) to the widely used UV-Vis absorption detection.

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Section: Nonaqueous Cementioning

confidence: 99%

Sensitive chiral analysis by capillary electrophoresis

García-Ruiz

Marina

2006

Electrophoresis

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“…Another class of chiral additives has also been applied to the enantiomeric resolution in NACE, ion-pairing reagents such as camphorsulfonate (camphorSO 3 2 ), quinine, quinidine, other cinchona alkaloids and their derivatives, and (2)-2,3:4,6-di-O-isopropylidene-2-keto-L -gulonic acid [20][21][22][23]. Recently, Hedeland et al [24] introduced N-benzoxycarbonylglycyl-L -proline as chiral counterion for the enantioseparation of amines in methanol mixed with different percentages of dichloromethane, 1,2-dichloroethane or 2-propanol containing ammonium acetate.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of basic compounds using heptakis(2,3‐di‐O‐methyl‐6‐O‐sulfo)‐β‐cyclodextrin in combination with potassium camphorsulfonate in nonaqueous capillary electrophoresis: Optimization by means of an experimental design

et al. 2004

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The enantiomeric separation of a series of basic pharmaceuticals (beta-blockers, local anesthetics, sympathomimetics) has been investigated in nonaqueous capillary electrophoresis (NACE) systems using heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-cyclodextrin (HDMS-beta-CD) in combination with potassium camphorsulfonate (camphorSO3-). For this purpose, a face-centered central composite design with 11 experimental points was applied. The effect of the concentrations of HDMS-beta-CD and camphorSO3- on enantioresolution was statistically evaluated and depended largely on the considered analyte. The presence of camphorSO3- was found to be particularly useful for the enantioseparation of compounds with high affinity for the anionic CD. CamphorSO3- seems to act as a competitor, reducing the affinity for the CD, probably by ion-pair formation with these analytes. For compounds with lower affinity for HDMS-beta-CD, the combination of camphorSO3- and the CD appeared to have a favorable effect on enantioresolution only if the optimal CD concentration could be reached. On the other hand, for compounds characterized by a very low affinity for the anionic CD, the association of camphorSO3- and HDMS-beta-CD is always unfavorable. Finally, experimental conditions were selected by means of the multivariate approach in order to obtain the highest resolution (Rs) value for each studied compound.

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“…Quinine [83], tert-butyl carbamoylated quinine and other cinchona alkaloids and derivatives were also investigated for the chiral separation of N-protected amino acids [84][85][86][87]. Higher enantioselectivity was observed using the cinchona alkaloid derivatives, especially those with a carbamate function [85].…”

Section: Chiral Ion-pairing Reagentsmentioning

confidence: 99%

“…Higher enantioselectivity was observed using the cinchona alkaloid derivatives, especially those with a carbamate function [85]. Moreover, the presence of a bulky substituent on the carbamoylated derivatives or the use of dimeric forms of carbamoylated quinine and quinidine derivatives had a favorable effect on the enantioselectivity [86,87]. In addition, N-protected amino acids, like (R)-and (S)-3,5-dinitrobenzoyl-leucine, can also be used as chiral ion-pairing reagent for the enantioseparation of cinchona alkaloids and structurally related compounds [88].…”

Section: Chiral Ion-pairing Reagentsmentioning

confidence: 99%