A total of 26 different cyclodextrin (CD) derivatives with different functional groups and degrees of substitution were tested against 35 basic pharmaceutical compounds in an effort to investigate their effectiveness as chiral selectors for enantiomeric separation in capillary electrophoresis (CE). Testing was performed under the same conditions using a low pH buffer (25 mM phosphate buffer at pH approximately 2.5). Five CD derivatives, namely, highly sulfated-beta-CD, highly sulfated-beta-CD, hydroxypropyl-beta-CD (degree of substitution approximately 1), heptakis-(2,6-O-dimethyl)-beta-CD, and heptakis(2,3,6-O-trimethyl)-beta-CD were identified to be most effective for enantiomeric separations and have a wide range of enantiomeric selectivity towards the model compounds. Over 90% of the model compounds were enantiomerically resolved with the five identified CD derivatives, at a minimum resolution of 0.5. An additional 20 compounds were also tested to demonstrate the validity of the identified CD derivatives. The five CD derivatives were recommended as the starting chiral selectors in developing enantiomeric separation methods by CE.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/s0021-9673(02)01192-5 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Recent Advances in Enantiorecognition and Enantioseparation Techniques of Chiral Molecules in the Pharmaceutical Field.
Biomed Chromatogr
February 2025
Department of Pharmaceutical Chemistry and Analysis, ISF College of Pharmacy, Moga, Punjab, India.
Enantioseparation and enantiorecognition are crucial in the pharmaceutical analysis of chiral substances, impacting safety, efficacy, and regulatory compliance. Enantioseparation refers to the process of separating enantiomers from a mixture, typically achieved through chromatography techniques like HPLC and SFC. In contrast, enantiorecognition involves the identification of enantiomers based on their interaction with a chiral selector without the need for separation.
View Article and Find Full Text PDFPreparation of a 1,1'-Binaphthyl-based Chiral Polyimine Macrocycle Bonded Chiral Stationary Phase by Thiol-ene Click Reaction and Its Enantioseparation Performance in High-Performance Liquid Chromatography.
J Sep Sci
December 2024
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, China.
Chiral macrocycles have emerged as attractive media for chromatographic enantioseparation due to their excellent host-guest recognition properties. In this study, a new chiral stationary phase (CSP) based on 1,1'-binaphthyl chiral polyimine macrocycle (CPM) was reported. The CPM was synthesized by one-step aldehyde-amine condensation of (S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxaldehyde with 1,2-phenylenediamine and bonded on thiolated silica via the thiol-ene click reaction to afford the CSP.
View Article and Find Full Text PDFCyclodextrins-based deep eutectic supramolecules as chiral selectors for enhanced enantioseparation in capillary electrophoresis.
J Chromatogr A
January 2025
Department of Pharmacy, Affiliated Hospital of Nantong University, No.20 Xisi Road, Nantong, Jiangsu 226001, PR China. Electronic address:
The joint use of deep eutectic solvents (DESs) and cyclodextrins (CDs) has been well demonstrated to have a promoting effect on chiral separation in capillary electrophoresis (CE). These studies focused on constructing synergistic separation systems by adding DESs and CDs to the buffer solution respectively. In this work, for the first time, β-cyclodextrin (β-CD), methyl-β-cyclodextrin (M-β-CD), and hydroxypropyl-β-cyclodextrin (HP-β-CD) were directly used as precursors to prepare several CDs-based deep eutectic supramolecules (DESUPs) by assembling with two organic acids (L-lactic acid and L-malic acid) in different ratios through a simple two-phase mixing.
View Article and Find Full Text PDFChiral Cobalt Nanocluster-Driven Chemiluminescent System for the Facile Discrimination of Carnitine Enantiomers with a Hydrogel-Assisted Strategy.
Anal Chem
December 2024
Key Laboratory of Luminescence Analysis and Molecular Sensing (Ministry of Education), College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, China.
Facile chiral discrimination without relying on chromatographic techniques has long been a huge challenge due to the minimal differences in the physicochemical properties of enantiomers. Polysaccharide hydrogels with natural chiral selectivity can be promising materials for constructing chiral discrimination platforms. In this study, l-cysteine-induced cobalt nanoclusters (LC-CoNCs) were prepared and utilized as chiral nanozymes for promoting the chemiluminescent (CL) signal of a luminol-HO system.
View Article and Find Full Text PDFDetermination of the Effective Charge Numbers and Ionic Mobilities of Single Isomer and Randomly Highly Sulfated Cyclodextrins by Capillary Isotachophoresis and Zone Electrophoresis.
Electrophoresis
November 2024
Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Prague, Czech Republic.
Article Synopsis
- Sulfated cyclodextrins are negatively charged molecules used in capillary electrophoresis for separating chiral compounds, but their effective charge can be lower than expected due to counterion binding.
- This study used capillary isotachophoresis and capillary zone electrophoresis to measure the effective charge numbers and ionic mobilities of two types of sulfated cyclodextrins: single isomer and randomly highly sulfated.
- Results showed that while the effective charge numbers of single isomer sulfated cyclodextrins closely matched their sulfate groups, the randomly highly sulfated versions had their effective charges reduced by 22.2%-27.8%, leading to lower ionic mobilities for the single isomer
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!