Nonaqueous capillary electrophoretic separation of basic enantiomers using heptakis(2,3-dimethyl-6-sulfato)-β-cyclodextrin

Tacker, Matthew; Glukhovskiy, Pavel; Cai, Hong; Vigh, Gyula

doi:10.1002/(sici)1522-2683(19990901)20:13<2794::aid-elps2794>3.0.co;2-4

Cited by 53 publications

(22 citation statements)

References 29 publications

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“…Similarly to the m EO values observed earlier with HDAS [12] and HDMS [13,14], the m EO values decreased from about 14610 -5 cm 2 V -1 s -1 at 0 mM to about 4610 -5 cm 2 V -1 s -1 at 40 mM ODMS concentrations. These m EO values led to reasonably fast weak-base enantiomer separations.…”

Section: Resultssupporting

confidence: 83%

“…However, the randomly sulfated CDs are not sufficiently soluble in pure methanol or acetonitrile, the preferred UV-transparent NACE solvents. Some of the single-isomer sulfated CDs, on the other hand, such as heptakis(2,3-O-diacetyl-6-O-sulfo)-CD (HDAS) [12], heptakis(2,3-O-dimethyl-6-O-sulfo)-b-CD (HDMS) [13,14] and octakis(2,3-O-diacetyl-6-O-sulfo)-g-CD (ODAS) [15] are soluble in methanol at concentrations as high as 40 mM and, consequently, were used successfully for the NACE separation of weak-base enantiomers. Recently, we described the synthesis and first use, in aqueous BGEs, of the latest single-isomer, sulfated CD derivative, octakis(2,3-O-dimethyl-6-O-sulfo)-g-CD (ODMS) (Busby and Vigh, submitted).…”

Section: Introductionmentioning

confidence: 99%

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Nonaqueous capillary electrophoretic separation of basic enantiomers using octakis(2,3-O-dimethyl-6-O-sulfo)-γ-cyclodextrin, a new, single-isomer chiral resolving agent

2002

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The enantiomers of 34 pharmaceutical weak-base analytes were separated by nonaqueous capillary electrophoresis in acidic methanol background electrolytes using the sodium salt of the new, single-isomer chiral resolving agent, octakis(2,3-O-dimethyl-6-O-sulfo)-gamma-cyclodextrin (ODMS). The effective mobilities, separation selectivities and peak resolution values of the weak-base analytes were determined as a function of the ODMS concentration in the 0-40 mM range and were found to follow the theoretical predictions of the charged resolving agent migration model (CHARM model) modified for ionic strength effects. Fast, efficient separations were achieved for both comparatively small and large enantiomers.

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Section: Resultssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Nonaqueous capillary electrophoretic separation of basic enantiomers using octakis(2,3-O-dimethyl-6-O-sulfo)-γ-cyclodextrin, a new, single-isomer chiral resolving agent

2002

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“…Particularly ion-pairing interactions become strong in acetonitrile and alcohols and in these media the classical ion-pairing resolving agents like quinine based selectors (for enantiomeric anions) [91, 92, 190±194] and camphorsulfonates (for enantiomeric cations) [195] can be employed. However, also CD-based neutral and charged selectors have been successfully applied [138,139,141,196,197], as well as ligand-pairs [198]. Other solvents, such as formamide, N-methylformamide, N,N-dimethylformamide, dimethylsulfoxide, ethyl acetate and tetrahydrofuran have been used as nonaqueous media (BGE), too [199].…”

Section: Organic Solvent Components and Nonaqueous Systemsmentioning

confidence: 99%

Fundamental aspects of chiral separations by capillary electrophoresis

2001

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A review is presented that surveys the basic theory of direct separation of enantiomers by capillary electrophoretic (CE) techniques. These separations are based on the formation of diastereomeric complexes between the enantiomeric analytes and a chiral selector added to the electrolyte solution. The review covers a comprehensive treatment of the equations needed for optimization of selectivity coefficients, resolution and analysis time in the zone electrophoretic mode. In this context, it takes into account combined equilibria of complexation and protonation/deprotonation as well as complexation and paritition into micelles. On the basis of these equations, the benefits of charged selectors and the optimization potential inherent to pH tuning can be documented. In addition, the review deals with some basic aspects of chiral isoelectric focusing and briefly discusses indirect enantioseparation. In a subsequent section a survey is given on particularfeatures of the various types of chiral selectors. Finally, the recent developments in preparative enantioseparation in continuous free-flow system and by use of isoelectric membranes are discussed.

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“…However, it is not always a desirable medium in CE or CEC separations, due to limited solubility or stability of analytes, for instance hydrophobic and weak electrolytes [39,246], or/and additives such as b-CD [58], in aqueous solvents. Furthermore, use of nonaqueous BGE is a promising alternative for chiral selectors that cannot exhibit a desirable enantioselectivity in water-based background electrolytes, owing to a very strong hydrophobic interaction with analyte.…”

Section: Generalmentioning

confidence: 99%

“…This means that NACE improves the solubility of the chiral selector at the expense of increasing the optimal chiral selector concentration. Despite that, NACE extends the applicability of CE to hydrophobic chiral selectors and neutral or weak electrolyte, for example, enantiomeric separation of weak base with octakis(2,3-diacetyl-6-sulfo)-g-CD as chiral selector or single isomeric heptakis(2,3-dimethyl-6-sulfo)-b-CD [246] in acidic methanol [39,250]. It is noteworthy that CD-MEKC [169,170] and microemulsion EKC have been used to separate hydrophobic enantiomers and to employ hydrophobic chiral selectors, for instance, d-nbutyl tartrate [251], respectively.…”

Section: Generalmentioning

confidence: 99%

Recent developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis

Ahmad

2001

Electrophoresis

186

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This paper provides an overview of the current status of chiral capillary electrophoresis (CE). The emphasis is placed on the application of CE in chiral separation of various racemic compounds. During the last two years about 280 papers, several review articles, and two entire issues, edited by S. Fanali (Electrophoresis 1999, 20, 2577-2798, and H. Nishi and S. Terabe (J. Chromatogr. A 2000, 879, 1-471.) have been devoted to chiral CE. Enantiomeric separations of various compounds, e.g., pharmaceuticals, drug candidates, drugs and related metabolites in biological fluids, amino acids, di- and tri peptides, pesticides and fungicides, have been performed using different chiral selectors. Native and derivatized cyclodextrins continue to be the most widely used chiral selectors. Other chiral selectors such as natural and synthetic chiral micelles, crown ethers, chiral ligands, proteins, oligo- and polysaccharides, and macrocyclic antibiotics have also been applied to chiral CE separations.

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Nonaqueous capillary electrophoretic separation of basic enantiomers using heptakis(2,3-dimethyl-6-sulfato)-β-cyclodextrin

Cited by 53 publications

References 29 publications

Nonaqueous capillary electrophoretic separation of basic enantiomers using octakis(2,3-O-dimethyl-6-O-sulfo)-γ-cyclodextrin, a new, single-isomer chiral resolving agent

Nonaqueous capillary electrophoretic separation of basic enantiomers using octakis(2,3-O-dimethyl-6-O-sulfo)-γ-cyclodextrin, a new, single-isomer chiral resolving agent

Fundamental aspects of chiral separations by capillary electrophoresis

Recent developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis

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