Chromatographic Chiral Separation

2010 ◽  
pp. 249-252
Keyword(s):  
2001 ◽  
Vol 24 (5) ◽  
pp. 402-406 ◽  
Author(s):  
Kyeong Ho Kim ◽  
Joo Hyun Lee ◽  
Mi Young Ko ◽  
Seon-Pyo Hong ◽  
Jeong Rok Youm

Heliyon ◽  
2021 ◽  
pp. e07707
Author(s):  
Suci Amalia ◽  
Stevin Carolius Angga ◽  
Elvina Dhiaul Iftitah ◽  
Dias Septiana ◽  
Baiq Octaviana D. Anggraeny ◽  
...  

2021 ◽  
Vol 22 (13) ◽  
pp. 7139
Author(s):  
Wojciech Bocian ◽  
Elżbieta Bednarek ◽  
Katarzyna Michalska

Molecular modeling (MM) results for tedizolid and radezolid with heptakis-(2,3-diacetyl-6-sulfo)-β-cyclodextrin (HDAS-β-CD) are presented and compared with the results previously obtained for linezolid and sutezolid. The mechanism of interaction of chiral oxazolidinone ligands belonging to a new class of antibacterial agents, such as linezolid, tedizolid, radezolid, and sutezolid, with HDAS-β-CD based on capillary electrokinetic chromatography (cEKC), nuclear magnetic resonance (NMR) spectroscopy, and MM methods was described. Principles of chiral separation of oxazolidinone analogues using charged single isomer derivatives of cyclodextrin by the cEKC method were presented, including the selection of the optimal chiral selector and separation conditions, complex stoichiometry, and binding constants, which provided a comprehensive basis for MM studies. In turn, NMR provided, where possible, direct information on the geometry of the inclusion complexes and also provided the necessary structural information to validate the MM calculations. Consequently, MM contributed to the understanding of the structure of diastereomeric complexes, the thermodynamics of complexation, and the visualization of their structures. The most probable mean geometries of the studied supramolecular complexes and their dynamics (geometry changes over time) were determined by molecular dynamics methods. Oxazolidinone ligands have been shown to complex mainly the inner part of cyclodextrin, while the external binding is less privileged, which is consistent with the conclusions of the NMR studies. Enthalpy values of binding of complexes were calculated using long-term molecular dynamics in explicit water as well as using molecular mechanics, the Poisson–Boltzmann or generalized Born, and surface area continuum solvation (MM/PBSA and MM/GBSA) methods. Computational methods predicted the effect of changes in pH and composition of the solution on the strength and complexation process, and it adapted the conditions selected as optimal during the cEKC study. By changing the dielectric constant in the MM/PBSA and MM/GBSA calculations, the effect of changing the solution to methanol/acetonitrile was investigated. A fairly successful attempt was made to predict the chiral separation of the oxazolidinones using the modified cyclodextrin by computational methods.


Molecules ◽  
2019 ◽  
Vol 24 (6) ◽  
pp. 1135 ◽  
Author(s):  
Raymond B. Yu ◽  
Joselito P. Quirino

Chiral separation is an important process in the chemical and pharmaceutical industries. From the analytical chemistry perspective, chiral separation is required for assessing the fit-for-purpose and the safety of chemical products. Capillary electrophoresis, in the electrokinetic chromatography mode is an established analytical technique for chiral separations. A water-soluble chiral selector is typically used. This review therefore examines the use of various chiral selectors in electrokinetic chromatography during 2017–2018. The chiral selectors were both low and high (macromolecules) molecular mass molecules as well as molecular aggregates (supramolecules). There were 58 papers found by search in Scopus, indicating continuous and active activity in this research area. The macromolecules were sugar-, amino acid-, and nucleic acid-based polymers. The supramolecules were bile salt micelles. The low molecular mass selectors were mainly ionic liquids and complexes with a central ion. A majority of the papers were on the use or preparation of sugar-based macromolecules, e.g., native or derivatised cyclodextrins. Studies to explain chiral recognition of macromolecular and supramolecular chiral selectors were mainly done by molecular modelling and nuclear magnetic resonance spectroscopy. Demonstrations were predominantly on drug analysis for the separation of racemates.


1998 ◽  
Vol 21 (2) ◽  
pp. 212-216 ◽  
Author(s):  
Kyeong Ho Kim ◽  
Hyeong Won Yun ◽  
Hyun Ju Kim ◽  
Hyun Ji Park ◽  
Pok Wha Choi

Chirality ◽  
2017 ◽  
Vol 29 (9) ◽  
pp. 558-565 ◽  
Author(s):  
Zhaokun Wang ◽  
Qiongwen Zhang ◽  
Linda Luo ◽  
Tiemin Sun ◽  
Xingjie Guo

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