Direct enantiomeric separations by high performance liquid chromatography using cyclodextrins

Han, Soon M.

doi:10.1002/(sici)1099-0801(199709)11:5<259::aid-bmc701>3.0.co;2-u

Cited by 101 publications

(23 citation statements)

References 112 publications

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“…The increasing demand for chiral compounds in chemical, biological, and pharmaceutical fields has driven not only the development of asymmetric synthetic methodologies for obtaining chiral compounds in high yields but also the development of rapid, convenient, and accurate methodologies for measuring the optical purities of chiral compounds via multivariate analytical technologies, such as HPLC, 1 GC, 2 CE, 3 NMR, 4 etc. Among these methods, NMR spectroscopy using chiral solvating agents (CSAs) to form diastereomeric complexes with samples via noncovalent interactions might be one of the most facile methods without chiral derivatization of the analyte or using special equipment apart from the common NMR spectrometers, which has the advantages of easy performance and accessibility.…”

Section: ■ Introductionmentioning

confidence: 99%

A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP

et al. 2013

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A simple chiral bisthiourea has been used as a highly effective and practical chemical solvating agent (CSA) for diverse α-carboxylic acids in the presence of DMAP. Excellent enantiodiscrimination based on well-resolved α-H NMR signals of the enantiomers of carboxylic acids can be obtained without interference from the chiral bisthiourea and DMAP. To check the practicality of the chiral bisthiourea/ DMAP for enantiomeric determination, the ee values of mandelic acid (MA) samples over a wide ee range were determined by integration of the α-H signal of MA in 1 H NMR. A discrimination mechanism is proposed, that the formation of two diasteromeric ternary complexes between the chiral bisthiourea and two in situ formed enantiomeric carboxylate-DMAPH + ion pairs discriminates the enantiomers of carboxylic acids. Computational modeling studies show that the chemical shift value of α-H of (S)-MA is greater than that of (R)-MA in ternary complexes, which is consistent with experimental observation. 1D and 2D NOESY spectra demonstrate the intermolecular noncovalent interactions between the protons on the aromatic rings of chiral bisthiourea and α-H of the enantiomers of racemic α-methoxy phenylacetic acids in the complexes.

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Section: ■ Introductionmentioning

confidence: 99%

A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP

et al. 2013

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“…Hence, taking into account the unique properties of cyclodextrins to generate hydrophobic cavities with hydrophilic exterior faces in aqueous solutions, the chiral discrimination between R-LC and S-LC will be due to the differences in their steric fit in the chiral cavities and their ability to establish hydrogen bonds. However, other intermolecular interactions may contribute for the enantiomeric resolution [18,20].…”

Section: Resultsmentioning

confidence: 99%

“…Since cyclodextrins have been widely used as chiral selectors [18] and a LiChroCART 250-4 ChiraDex (␤-cyclodextrin, 5 m) column has been used to separate ESL metabolites (S-LC, R-LC and OXC) by LC-MS using water/methanol (80:20, v/v) at a flow rate of 0.8 mL min −1 [6,14], these chromatographic conditions coupled to UV detection at 210 nm [8] were predefined for the first experiments. However, under these conditions, the resolution between R-LC and S-LC was not enough.…”

Section: Methods Development and Selectivitymentioning

confidence: 99%

Simultaneous and enantioselective liquid chromatographic determination of eslicarbazepine acetate, S-licarbazepine, R-licarbazepine and oxcarbazepine in mouse tissue samples using ultraviolet detection

Alves

Figueiredo

Castel‐Branco

et al. 2007

Analytica Chimica Acta

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Herein is reported, for the first time, a simple and reliable chiral reversed-phase liquid chromatographic method coupled to ultraviolet (UV) detection for simultaneous determination of eslicarbazepine acetate (ESL) and its metabolites, S-licarbazepine (S-LC), R-licarbazepine (R-LC) and oxcarbazepine (OXC), in mouse plasma and brain, liver and kidney tissue homogenates. All analytes and the internal standard were extracted from plasma and tissue homogenates by a solid-phase extraction procedure using Waters Oasis ® hydrophilic-lipophilic balance cartridges. The chromatographic separation was performed by isocratic elution with water/methanol (88:12, v/v), pumped at a flow rate of 0.7 mL min −1 , on a Lichro-CART 250-4 ChiraDex (␤-cyclodextrin, 5 m) column at 30• C. The UV detector was set at 225 nm. Calibration curves were linear (r 2 ≥ 0.996) in the ranges 0.4-8 g mL −1 , 0.1-1.5 g mL −1 and 0.1-2 g mL −1 for ESL and OXC and in the ranges 0.4-80 g mL −1 , 0.1-15 g mL −1 and 0.1-20 g mL −1 for R-LC and S-LC in plasma, brain and liver/kidney homogenates, respectively. The overall precision not exceeded 11.6% (%CV) and the accuracy ranged from −3.79 to 3.84% (%bias), considering all analytes in all matrices. Hence, this method will be a useful tool to characterize the pharmacokinetic disposition of ESL in mice.

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“…[1][2][3] Therefore, they are used for increasing the solubility and separation factor of many organic compounds. However, only little has been reported concerning inclusion complexes of organic compounds with a CD polymer as a guest molecule, because it was not dissolved in common organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of Cyclodextrin Polymer and Its High-Performance Liquid-Chromatography Stationary Phase

et al. 2002

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Cyclodextrin (CD) polymers were synthesized from the reaction of native CDs with a hexamethylene diisocyanate (HDI) compound in a dried DMF solution. The obtained CD polymer contained a range of 8 -14% N due to HDI by elemental analysis. The physical and chemical properties of the CD polymers were characterized by IR, solid state 13 C NMR, TGA, and DSC, respectively. An HPLC column was prepared using the CD polymer with a carbamate linker by a slurry method. Separation of the phenol isomers was conducted using the CD polymer stationary phase and CD by HPLC. Furthermore, an inclusion complex of the phenol isomer was studied by FT-Raman spectroscopy. From the HPLC and FT-Raman results, inclusion phenomena of o-, m-, and p-nitrophenol onto CD and CD polymers were analyzed.

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Direct enantiomeric separations by high performance liquid chromatography using cyclodextrins

Cited by 101 publications

References 112 publications

A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP

A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP

Simultaneous and enantioselective liquid chromatographic determination of eslicarbazepine acetate, S-licarbazepine, R-licarbazepine and oxcarbazepine in mouse tissue samples using ultraviolet detection

Preparation and Characterization of Cyclodextrin Polymer and Its High-Performance Liquid-Chromatography Stationary Phase

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