Chromatographic enantioseparation and adsorption thermodynamics of hydroxy acids and their derivatives on antibiotic-based chiral stationary phases as affected by eluent pH

Gogolishvili, Otar Sh.; Reshetova, E. N.

doi:10.1007/s10337-020-03978-w

Cited by 9 publications

(3 citation statements)

References 49 publications

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“…1367,1368 Recently, a series of interesting studies on the application of adsorption methods for mechanistic studies on enantioselective selector−selectand interactions in chromatography were published by Asnin's, 1369 Tsui's, 1370,1371 Felinger's, 1224 Cavazzini's, 1372,1373 and a few other groups. 1374 Just a very few of these studies are briefly summarized below, whereas earlier studies on this topic were summarized by Asnin. 1375 Asnin and co-workers studied the dynamics of adsorption of the stereoisomers of the dipeptide Leu-Leu in a chromatographic column packed with the CSP bearing antibiotic ristocetin A attached to the silica.…”

Section: Nuclear Magnetic Resonancementioning

confidence: 99%

“…Recently, a series of interesting studies on the application of adsorption methods for mechanistic studies on enantioselective selector–selectand interactions in chromatography were published by Asnin’s, Tsui’s, , Felinger’s, Cavazzini’s, , and a few other groups . Just a very few of these studies are briefly summarized below, whereas earlier studies on this topic were summarized by Asnin .…”

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

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Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

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Section: Nuclear Magnetic Resonancementioning

confidence: 99%

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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“…The xanthone derivatives could be separated with good selectivities and resolutions on at least one column, while the docking study showed different binding patterns for each selector due to their complex structures. The enantioseparation and adsorption thermodynamics of aromatic hydroxy acids and their derivatives on Nautilus-E, Nautilus-R (Biokhimmak, Moscow, Russia), and Chirobiotic T was investigated [ 35 ]. Different retention and enantiorecognition mechanisms on eremomycin and ristomycin were found compared to teicoplanin.…”

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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Fast, sensitive LC–MS resolution of $${{\upalpha}}$$-hydroxy acid biomarkers via SPP-teicoplanin and an alternative UV detection approach

Aslani,

Armstrong

2024

Anal Bioanal Chem

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Chromatographic enantioseparation and adsorption thermodynamics of hydroxy acids and their derivatives on antibiotic-based chiral stationary phases as affected by eluent pH

Cited by 9 publications

References 49 publications

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

Fast, sensitive LC–MS resolution of $${{\upalpha}}$$-hydroxy acid biomarkers via SPP-teicoplanin and an alternative UV detection approach

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