Enantioselective potential of teicoplanin- and vancomycin-based superficially porous particles-packed columns for supercritical fluid chromatography

Folprechtová, Denisa; Kozlov, Oleksandr; Armstrong, Daniel W.; Schmid, Martin G.; Kalíková, Květa; Tesařová, Eva

doi:10.1016/j.chroma.2019.460687

Cited by 20 publications

(22 citation statements)

References 64 publications

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“…The Teicoshell column exhibits higher enantiorecognition ability than the Vancoshell column for a group of structurally different synthetically modified indole phytoalexins and tryptophan derivatives. On the other hand, the Vancoshell column provides higher enantioselective potential for chiral calcium channel blockers than the Teicoshell column under the same conditions 74 . In this work, complementary enantioseparation behavior of teicoplanin and vancomycin‐based CSPs was confirmed.…”

Section: Applicationssupporting

confidence: 56%

“…Methanol (with or without additives) is the most often used co‐solvent to increase the elution strength of the MP with MG‐based CSPs in SFC 73 . A few works dealing with the effect of co‐solvent type on retention and enantioseparation on MG‐based CSPs can be found in the literature 74,75 . The TeicoShell (teicoplanin as CS), the VancoShell (vancomycin as CS), the TagShell (teicoplanin aglycone as CS), and the NicoShell (modified MG as CS) columns were tested for their enantioselectivity for rod‐like liquid crystals 75 .…”

Section: Theoretical Studies Of Macrocyclic Glycopeptides In Sfcmentioning

confidence: 99%

“…The results showed that polysaccharide‐based CSPs provide generally better enantioseparation and higher enantioselectivity for these liquid crystals compared to MG‐based CSPs. Other work compares enantioselective potential of TeicoShell and VancoShell columns for various groups of chiral analytes, that is, phytoalexins, ketamine, and cathinone derivatives, 76 substituted tryptophans, and calcium channel blockers 74 . The effect of co‐solvent type, that is, methanol, ethanol, propan‐2‐ol, and propan‐1‐ol on retention and enantioseparation were evaluated.…”

Section: Theoretical Studies Of Macrocyclic Glycopeptides In Sfcmentioning

confidence: 99%

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Macrocyclic glycopeptide‐based chiral selectors for enantioseparation in sub/supercritical fluid chromatography

Folprechtová

Kalíková

2020

Analytical Science Advances

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Increasing number of reported works dealing with macrocyclic glycopeptide‐based columns in sub/supercritical fluid chromatography (SFC) points to the growing interest in this area. With the development and production of sub 2 µm fully porous particles and superficially porous particles with bonded macrocyclic glycopeptides, significant improvements have been made in ultrafast high efficiency chiral SFC. This review article gives an overview of macrocyclic glycopeptide‐based chiral selectors that were used in theoretical studies and/or applications in SFC. The review covers the period from 1997 when macrocyclic glycopeptides were first used in SFC till the end of July 2020 according to Web of Science. This work can also be helpful to analysts searching for an appropriate method for the separation/determination of enantiomers of their interest.

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Section: Applicationssupporting

confidence: 56%

Section: Theoretical Studies Of Macrocyclic Glycopeptides In Sfcmentioning

confidence: 99%

Section: Theoretical Studies Of Macrocyclic Glycopeptides In Sfcmentioning

confidence: 99%

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Macrocyclic glycopeptide‐based chiral selectors for enantioseparation in sub/supercritical fluid chromatography

Folprechtová

Kalíková

2020

Analytical Science Advances

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“…Namely, better chromatographic efficiencies and often shorter retention times were obtained compared to methanol, especially with polar CSPs. The enantioseparation of biologically active and structurally diverse chiral compounds was investigated employing VancoShell and TeicoShell columns under SFC conditions [ 86 ]. The influence of mobile phase conditions on retention and enantioselectivity was examined, and complementary behavior of the macrocyclic antibiotic-based columns was confirmed.…”

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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“…Macrocyclic glycopeptide (MG)‐based chiral selectors (CSs) have been widely used in various separation techniques, i.e., liquid chromatography (LC), capillary electrophoresis, and sub/supercritical fluid chromatography (SFC) due to the broad enantioselectivity toward many chiral pharmaceuticals and biologically active compounds [1–13]. In addition, MG‐based chiral stationary phases (CSPs) are considered to be complementary to each other [2,14–17].…”

Section: Introductionmentioning

confidence: 99%

The effect of tandem coupling of NicoShell and TeicoShell columns in sub/supercritical fluid chromatography on enantioresolution

Folprechtová

Tesařová

Kalíková

2021

J of Separation Science

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The coupling of columns in sub/supercritical fluid chromatography presents a great opportunity for influencing the separation efficiency and extending the selectivity of the separation system. Combinations of different types of chiral stationary phases could positively affect the enantioresolution if single ones are complementary to each other. In this work, two superficially porous particle (2.7 μm) macrocyclic glycopeptide‐based columns, namely TeicoShell and NicoShell, were serially coupled and tested in sub/supercritical fluid chromatography for the first time. The influence of the column arrangement on the enantioseparation of structurally diverse biologically active compounds was examined. The obtained results showed how the column order crucially affected the enantioresolution of compounds tested, but the retention was negligibly affected in most cases. We also demonstrated that single TeicoShell and NicoShell columns are very promising towards the development of highly efficient and fast/ultrafast sub/supercritical fluid chromatography methods for structurally different chiral compounds. The optimized methods for sub‐minute enantioselective separation of certain biologically important compounds were proposed.

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Enantioselective potential of teicoplanin- and vancomycin-based superficially porous particles-packed columns for supercritical fluid chromatography

Cited by 20 publications

References 64 publications

Macrocyclic glycopeptide‐based chiral selectors for enantioseparation in sub/supercritical fluid chromatography

Macrocyclic glycopeptide‐based chiral selectors for enantioseparation in sub/supercritical fluid chromatography

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

The effect of tandem coupling of NicoShell and TeicoShell columns in sub/supercritical fluid chromatography on enantioresolution

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