Chiral separations of indan, tetralin and benzosuberan derivatives by capillary electrophoresis

Gahm, Kyung H.; Lee, Jauh Tzuoh; Chang, Lisa W.; Armstrong, Daniel W.

doi:10.1016/s0021-9673(97)00802-9

Cited by 11 publications

(7 citation statements)

References 29 publications

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“…[28][29][30] Succinyl-β-CD was excessively expensive in HPLC, and that's why it was not utilized in this experiment. Among the mobile phase additives employed in HPLC, CDs are the most successful ones in terms of enantioseparation because of their good solubility in aqueous solvents, low toxicity, and low UV absorption.…”

Section: Selection Of Suitable CD and Its Optimal Concentrationmentioning

confidence: 99%

“…In earlier reports, indanone and tetralone derivatives were separated by β-CD, CM-β-CD, and succinyl-β-CD using the CE method. [28][29][30] Succinyl-β-CD was excessively expensive in HPLC, and that's why it was not utilized in this experiment. Frequently used in HPLC, HP-β-CD was the third candidate in our study among all CDs and their derivatives.…”

Section: Selection Of Suitable CD and Its Optimal Concentrationmentioning

confidence: 99%

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Enantioseparation of nine indanone and tetralone derivatives by HPLC using carboxymethyl‐β‐cyclodextrin as the mobile phase additive

Guo

Sun

et al. 2016

Chirality

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High-performance liquid chromatography (HPLC) is a powerful method in the area of chiral separation. In this study, a method of HPLC using carboxymethyl-β-cyclodextrin (CM-β-CD) as chiral selector was developed for enantioseparation of nine indanone and tetralone derivatives. The separation was performed on a conventional C column. The optimal mobile phase was a mixture of methanol and 0.05 mol/L phosphate buffer at pH 1.8 (55:45, v/v) containing 22.9 mmol/L CM-β-CD. Under such conditions, the resolutions of all analytes were over 1.8 except for Compound F. The results of the study indicate the presence of a complex with 1:1 stoichiometry of the inclusion complex. In addition, it can be inferred from thermodynamic analysis that the behavior of formation of the inclusion complex and enantioseparation occurred simultaneously, while they were driven by different forces. The effect of analyte structure is also discussed.

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Section: Selection Of Suitable CD and Its Optimal Concentrationmentioning

confidence: 99%

Section: Selection Of Suitable CD and Its Optimal Concentrationmentioning

confidence: 99%

Enantioseparation of nine indanone and tetralone derivatives by HPLC using carboxymethyl‐β‐cyclodextrin as the mobile phase additive

Guo

Sun

et al. 2016

Chirality

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“…Since the nine anionic CDs tested (see Table 1) did not offer chiral discrimination for the glycidyl tosylate enantiomers, the possibility of using a dual system containing a neutral and a charged CD was studied. A combination of a neutral, often highly selective CD, with a poorly selective charged CD derivative, which provides an apparent electrophoretic mobility to the analyte, can be very useful to separate the enantiomers of neutral analytes [24][25][26][27][28][29]. From all the anionic CDs tested, Succ-b-CD showed the strongest interaction (the highest t mig /t EOF ratio) with the glycidyl tosylate enantiomers with the exception of carboxyethyl-b-cyclodextrin (Table 1).…”

Section: Choice Of the Chiral Selectormentioning

confidence: 99%

Enantiomeric separation of glycidyl tosylate by CE: Application to the study of catalytic asymmetric epoxidation of allyl alcohol

et al. 2008

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A CE method using CDs as chiral selectors was developed and validated to achieve the separation of glycidyl tosylate enantiomers originated by in situ derivatization of glycidol enantiomers obtained in asymmetric epoxidation of allyl alcohol with chiral titanium-tartrate complexes as catalysts. The effects of the nature, pH and concentration of the buffer, the nature and concentration of chiral selector, the addition of SDS, methanol, ethanol or 2-propanol, the capillary temperature, the effective capillary length and the applied voltage on the chiral resolution of glycidyl tosylate enantiomers were investigated. The best separation conditions were achieved using a Tris-borate buffer mixture (50 and 25 mM, respectively) at pH=9.3 with a dual CD system consisting of 2.5% succinyl-beta-CD and 1.0% beta-CD w/v at 15 degrees C. A baseline separation (resolution approximately 2.0) of the glycidyl tosylate enantiomers was obtained in a relatively short time (less than 12 min). Satisfactory results were obtained in terms of linearity (r>0.99) and intermediate precision (RSD below 8.5%). The LOD and LOQ were 3.0 and 10.0 mg/L, respectively, and the recoveries ranged from 99.8 to 108.8%. Finally, the method was applied to the determination of the enantiomeric excess and the yield obtained in the asymmetric epoxidation of allyl alcohol employing chiral titanium-tartrate complexes as catalysts after an in situ derivatization of glycidol enantiomers to glycidyl tosylate.

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“…Because additional pharmacological tests are currently performed on the 1-6 tetrahydronaphtalenic derivatives, the development of effective chiral analytical methods is needed: the other most widely used technique for chiral separations, CE, was then chosen as an alternative technique. Native and substituted CDs are the mostly used chiral selectors in CE and have previously made possible the baseline enantioresolution of tetralin derivatives: aminotetralins [10][11] and amidotetralins [12] were successfully enantioresolved by native and/or substituted CDs; neutral tetrahydronaphthalenic derivatives (analogs of 1-6) with nitrogen atom linked to the cycle through an alkyl chain was enantioresolved using highly sulfated CDs [13]. Our strategy was then based on the use of these anionic CDs to develop chiral analytical methods for 1-6.…”

Section: Introductionmentioning

confidence: 99%

Chiral resolution of melatoninergic ligands by EKC using highly sulfated CDs

et al. 2007

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EKC methods for the enantiomeric resolutions of melatoninergic ligands were developed using anionic CDs (highly S-alpha-CD, highly S-beta-CD, and highly S-gamma-CD) as chiral selectors at acidic pH 2.5. The optimization of the various operational parameters (nature and concentration of the CD, phosphate buffer concentration, addition of organic modifiers in the BGE, and temperature) allows baseline enantioresolutions (superior to 2) in short analysis times (inferior to 7 min) for all studied analytes. Some analytical characteristics of the optimal method were then studied for each analyte: repeatability, linearity, and LOD and LOQ. Lastly, determination of the apparent binding constants for the 18 complexes formed between the six analytes and the three CDs led us to rationalize the complexation mechanisms.

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Chiral separations of indan, tetralin and benzosuberan derivatives by capillary electrophoresis

Cited by 11 publications

References 29 publications

Enantioseparation of nine indanone and tetralone derivatives by HPLC using carboxymethyl‐β‐cyclodextrin as the mobile phase additive

Enantioseparation of nine indanone and tetralone derivatives by HPLC using carboxymethyl‐β‐cyclodextrin as the mobile phase additive

Enantiomeric separation of glycidyl tosylate by CE: Application to the study of catalytic asymmetric epoxidation of allyl alcohol

Chiral resolution of melatoninergic ligands by EKC using highly sulfated CDs

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