Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans.

Molecules

Interdisciplinary Excellence Centre, Institute of Pharmaceutical Analysis, University of Szeged, Somogyi u. 4, H-6720 Szeged, Hungary.

Published: July 2021

Natural compounds can exist in different forms, where molecules possessing chirality play an essential role in living organisms. Currently, one of the most important tasks of modern analytical chemistry is the enantioseparation of chiral compounds, in particular, the enantiomers of compounds having biological and/or pharmaceutical activity. Whether the task is to analyze environmental or food samples or to develop an assay for drug control, well-reproducible, highly sensitive, stereoselective, and robust methods are required. High-performance liquid chromatography best meets these conditions. Nevertheless, in many cases, gas chromatography, supercritical fluid chromatography, or capillary electrophoresis can also offer a suitable solution. Amino acids, proteins, cyclodextrins, derivatized polysaccharides, macrocyclic glycopeptides, and ion exchangers can serve as efficient selectors in liquid chromatography, and they are quite frequently applied and reviewed. Crown ethers and cyclofructans possessing similar structural characteristics and selectivity in the enantiodiscrimination of different amine compounds are discussed less frequently. This review collects information on enantioseparations achieved recently with the use of chiral stationary phases based on crown ethers or cyclofructans, focusing on liquid chromatographic applications.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8348247PMC
http://dx.doi.org/10.3390/molecules26154648DOI Listing

Publication Analysis

Top Keywords

crown ethers
12
ethers cyclofructans
12
liquid chromatographic
8
chiral stationary
8
stationary phases
8
phases based
8
based crown
8
liquid chromatography
8
liquid
4
chromatographic enantioseparations
4

Similar Publications

Recent progress using novel tetraphenylethylene-based macrocyclic hosts in water.

Chem Commun (Camb)

December 2024

Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, China.

Macrocyclic structures are popular in supramolecular chemistry and have enjoyed considerable success as platforms for elaboration to container compounds and new materials. Host/guest studies in organic media have relied heavily on structures derived from crown ethers, calixarenes, cucurbiturils, resorcinarenes and pillararenes over the past decades. More recently, their water-soluble versions have been developed for potential applications in biology.

View Article and Find Full Text PDF

Engineering Supramolecular [2]Daisy Chains for Structural Hierarchy-Dependent Emission and Photoreactivity.

J Am Chem Soc

December 2024

Key Laboratory of Structure and Functional Regulation of Hybrid Materials of Ministry of Education, Anhui Graphene Engineering Laboratory, Institutes of Physical Science and Information Technology, Anhui University, Hefei 230039, P. R. China.

Organic photofunctional materials exhibit properties that are highly dependent on their structural hierarchy. The variability in intermolecular interactions and molecular packing in both monomeric and aggregated states complicates the controllability and predictability of their photophysical and photochemical properties. To address this challenge, we developed three luminescent supramolecular [2]daisy chains as simplified models.

View Article and Find Full Text PDF

Background: Epidermal growth factor receptor tyrosine kinase inhibitor (EGFR-TKI) is considered highly effective treatment for advanced non-small cell lung cancer (NSCLC), who often develop drug resistance after 10 months of treatment. Herein, the aim was to unravel the mechanism behind the resistance to icotinib in NSCLC.

Methods: Establishment of icotinib-resistant PC-9 cells (PC-9R) was achieved through repeated exposure to increasing concentrations of icotinib for more than 12 months.

View Article and Find Full Text PDF

Unbuckling the 18-Crown-6 Ether Belt Around Metal Ions: Forging the Connection to the Condensed Phase.

J Am Chem Soc

November 2024

Department of Chemistry, School of Science, Institute of Science Tokyo, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550, Japan.

Crown ethers are central to supramolecular chemistry, recognizing and binding specific ions in solution. The most well-known, 18-Crown-6 (18C6), preferentially captures K in an aqueous solution, while gas phase binding of 18C6 with alkali metal ions decreases linearly with an increasing ionic radius. Why the high affinity for Li and Na in the gas phase is dramatically reduced with hydration remains an open question in understanding the K selectivity in the aqueous phase.

View Article and Find Full Text PDF

Nitrogen-containing macrocycles having a carbohydrate scaffold.

Adv Carbohydr Chem Biochem

November 2024

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. Electronic address:

Article Synopsis
  • Nitrogen-containing macrocyclic compounds like amines and amides are key focuses in supramolecular chemistry, particularly aza-macrocycles that include sugar units.
  • The article categorizes various types of carbohydrate-based macrocycles, including aza-crown ethers, cyclic oligomers from amino sugars, and nitrogen-containing glycophanes.
  • It also reviews strategies for creating these compounds and highlights their applications as important receptors in supramolecular chemistry.
View Article and Find Full Text PDF

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!