Unusual Difference in Enantioselectivity of Two Chiral Stationary Phases with Grafted Antibiotic Ristocetin A

Kopchenova, Margarita V.; Stepanova, Maria V.

doi:10.1007/s10337-021-04006-1

Cited by 7 publications

(3 citation statements)

References 11 publications

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“…Li et al reported a new preparation of teicoplanin-bonded CSP using the "thiol-ene" click reaction [89]. Additionally, some recent applications of macrocyclic antibiotic-based CSPs have also been reported [90][91][92].…”

Section: Macrocyclic Antibiotic-based Cspsmentioning

confidence: 99%

Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

Zhang

2021

J of Separation Science

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Separations and analyses of chiral compounds are important in many fields, including pharmaceutical production, preparation of chemical intermediates, and biochemistry. High-performance liquid chromatography using a chiral stationary phase is regarded as one of the most valuable methods for enantiomeric separation and analysis because it is highly efficient, is broadly applicable, and has powerful separation capability. The focus for development of this method is the identification of novel chiral stationary phases with superior recognition performance and good stability. The present article reviews recent progress in the development of new chiral stationary phases for high-performance liquid chromatography between January 2018 and June 2021. These newly reported chiral stationary phases are divided into three categories: small organic moleculebased (cyclodextrin and its derivatives, macrocyclic antibiotics, cinchona alkaloids, and other low molecular weight chiral molecules), macromoleculebased (cellulose and amylose derivatives, chitin and chitosan derivatives, and synthetic helical polymers) and chiral porous material-based (chiral metal-organic frameworks, chiral covalent organic frameworks, and chiral inorganic mesoporous silicas). Each type of chiral stationary phase is discussed in detail.

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Section: Macrocyclic Antibiotic-based Cspsmentioning

confidence: 99%

Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

Zhang

2021

J of Separation Science

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“…The enantioselective retention mechanisms employing dipeptides as model compounds were investigated on ristocetin-A-based CSPs by Asnin et al [ 62 , 63 , 64 ] under RP conditions. Effects of mobile phase composition on the separation of Ala–Ala, Leu–Leu, Gly–Leu, and Leu–Gly were studied on a Chirobiotic TM R column [ 62 ].…”

Section: Recent Applications Of Different Macrocyclic Antibiotic-based Cspsmentioning

confidence: 99%

“…The observed peculiarities of van Deemter plots were explained by the eddy dispersion, while the adsorption kinetics were found to have only secondary importance. A striking difference in the enantioselectivities of Chirobiotic TM R and Nautilus-R was observed in the enantiomeric separations of Ala–Ala, Gly–Leu, Leu–Gly [ 64 ]. Results were interpreted on the basis of the differing anchoring methods used to immobilize the selector onto the silica support, but the contribution of the structural variations of the binding sites to the observed phenomena could not be excluded.…”

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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Elucidation of retention mechanism of dipeptides on a ristocetin A-based chiral stationary phase using a combination of chromatographic and molecular simulation techniques

Varfaj

Pershina

Stepanova

et al. 2022

Journal of Chromatography A

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Unusual Difference in Enantioselectivity of Two Chiral Stationary Phases with Grafted Antibiotic Ristocetin A

Cited by 7 publications

References 11 publications

Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

Elucidation of retention mechanism of dipeptides on a ristocetin A-based chiral stationary phase using a combination of chromatographic and molecular simulation techniques

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