Chiral separation and modeling of quinolones on teicoplanin macrocyclic glycopeptide antibiotics <scp>CSP</scp>

Ali, Imran; Suhail, Mohd

doi:10.1002/chir.23024

Cited by 21 publications

(12 citation statements)

References 35 publications

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“…Regardless of the mobile phase employed, no chiral separation was observed on the macrocyclic glycopeptide-based columns. A method applying Chirobiotic TM T for the chiral resolution of quinolones was developed and described with mobile phases consisting of MeOH, MeCN, water, and TEA [ 55 ]. In addition to the chromatographic data, the supramolecular mechanism of the chiral recognition was established by a modeling study, where hydrogen bonds and π–π interactions were found to be the major forces in chiral separation.…”

Section: Recent Applications Of Different Macrocyclic Antibiotic-based Cspsmentioning

confidence: 99%

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

et al. 2021

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Numerous chemical compounds of high practical importance, such as drugs, fertilizers, and food additives are being commercialized as racemic mixtures, although in most cases only one of the isomers possesses the desirable properties. As our understanding of the biological actions of chiral compounds has improved, the investigation of the pharmacological and toxicological properties has become more and more important. Chirality has become a major issue in the pharmaceutical industry; therefore, there is a continuous demand to extend the available analytical methods for enantiomeric separations and enhance their efficiency. Direct liquid chromatography methods based on the application of chiral stationary phases have become a very sophisticated field of enantiomeric separations by now. Hundreds of chiral stationary phases have been commercialized so far. Among these, macrocyclic glycopeptide-based chiral selectors have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance. This review focuses on direct liquid chromatography-based enantiomer separations, applying macrocyclic glycopeptide-based chiral selectors. Special attention is paid to the characterization of the physico-chemical properties of these macrocyclic glycopeptide antibiotics providing detailed information on their applications published recently.

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Section: Recent Applications Of Different Macrocyclic Antibiotic-based Cspsmentioning

confidence: 99%

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

et al. 2021

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“…The theoretical study showed that each glycopeptide featured different patterns. Ali and co‐workers modelled the enantioseparation of four quinolones on teicoplanin by molecular docking, and HBs and π‐π interactions were found to be the major forces for chiral recognition .…”

Section: Miscellaneous Selectorsmentioning

confidence: 99%

Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

et al. 2019

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Liquid‐phase enantioseparations have been fruitfully applied in several fields of science. Various applications along with technical and theoretical advancements contributed to increase significantly the knowledge in this area. Nowadays, chromatographic techniques, in particular HPLC on chiral stationary phase, are considered as mature technologies. In the last thirty years, CE has been also recognized as one of the most versatile technique for analytical scale separation of enantiomers. Despite the huge number of papers published in these fields, understanding mechanistic details of the stereoselective interaction between selector and selectand is still an open issue, in particular for high‐molecular weight chiral selectors like polysaccharide derivatives. With the ever growing improvement of computer facilities, hardware and software, computational techniques have become a basic tool in enantioseparation science. In this field, molecular docking and dynamics simulations proved to be extremely adaptable to model and visualize at molecular level the spatial proximity of interacting molecules in order to predict retention, selectivity, enantiomer elution order, and profile noncovalent interaction patterns underlying the recognition process. On this basis, topics and trends in using docking and molecular dynamics as theoretical complement of experimental LC and CE chiral separations are described herein. The basic concepts of these computational strategies and seminal studies performed over time are presented, with a specific focus on literature published between 2015 and November 2018. A systematic compilation of all published literature has not been attempted.

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“…The simulation study is also very helpful in understanding the reaction mechanism and organic synthesis [32][33][34][35][36][37][38][39][40][41]. In the present work, the Milliken atomic charge in coulomb's acquired by an oxygen atom in different chemical species taken for the Cannizzaro reaction [25] was calculated by DFT method in the ground state by using the Gaussian(R) 03 program [42].…”

Section: The Density Functional Theory Studiesmentioning

confidence: 99%

Theoretical DFT study of Cannizzaro reaction mechanism: A mini perspective

et al. 2020

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In regards to the Cannizzaro reaction and its peculiar mechanism, some researchers have presented a free radical mechanism for the Cannizzaro reaction, while others have found that it is feasible through an ionic mechanism, but the actual mechanism has not been finalized yet. The researchers have given the proof of both the mechanisms through their papers published. Actually, Cannizzaro reaction may occur through both mechanisms depending on both molecular structure and different conditions which are yet to be explained. Recently published papers describe that free radical mechanism occurs only in a heterogeneous medium, while an ionic mechanism occurs in a homogeneous medium. We revealed no explanation of the molecular structure-based reason, responsible for a radical or an ionic mechanism. The present paper reviews not only homogeneous/heterogeneous medium conditions but also molecular structure-based facts, which may be responsible for the Cannizzaro reaction to occur through the radical or ionic mechanism, and that may be acceptable to the scientific society. Besides, Density Functional Theory study using Gaussian software was also involved in the explanation of the molecular structure, responsible for one of the two mechanisms. Also, the present paper specifies all points related to future perspectives on which additional studies are required to understand the actual mechanism with a definite molecular structure in the different reaction media.

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Chiral separation and modeling of quinolones on teicoplanin macrocyclic glycopeptide antibiotics CSP

Cited by 21 publications

References 35 publications

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

Theoretical DFT study of Cannizzaro reaction mechanism: A mini perspective

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