Enantioselective retention mechanisms of dipeptides on antibiotic-based chiral stationary phases: Leucyl-leucine, glycyl-leucine, and leucyl-glycine as case studies

Reshetova, E. N.; Kopchenova, Margarita V.; Vozisov, Stepan E.; Vasyanin, A. N.

doi:10.1016/j.chroma.2019.06.025

Cited by 15 publications

(5 citation statements)

References 28 publications

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“…For example, for Leu‐Leu, Δp K falls from 4.6 (water) to 2.6 (80% MeOH) (see Supporting Information to ref. [35]) 40 . Ionization will be still more suppressed in pure methanol.…”

Section: Resultsmentioning

confidence: 99%

Chiral separation of dipeptides on Cinchona‐based zwitterionic chiral stationary phases under buffer‐free reversed‐phase conditions

et al. 2022

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Chiral zwitterion ion exchangers represent efficient chiral stationary phases for stereoselective resolution of various analytes including chiral acids, bases, and zwitterions. In this contribution, we have focused on utilization of chiral zwitterionic sorbents, denoted as ZWIX (+A) and ZWIX (−A). These are analogical chiral systems to commercially available columns, Chiralpak ZWIX (+) and Chiralpak ZWIX (−), which are usually operated with buffered mobile phases. In this contribution, we have studied the enantiorecognition power of the ZWIX (+A) and ZWIX (−A) columns on a series of dipeptides operated under buffer‐free reversed‐phase conditions. Retention characteristics of zwitterionic dipeptides are discussed using an electrostatically driven adsorption model, which provides a good fit with both monotonous and U‐shaped curves.

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“…For example, for Leu‐Leu, Δp K falls from 4.6 (water) to 2.6 (80% MeOH) (see Supporting Information to ref. [35]) 40 . Ionization will be still more suppressed in pure methanol.…”

Section: Resultsmentioning

confidence: 99%

Chiral separation of dipeptides on Cinchona‐based zwitterionic chiral stationary phases under buffer‐free reversed‐phase conditions

et al. 2022

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“…The enantiomer elution order was studied by circular dichroism spectroscopy and quantum chemical approach. Chromatographic behaviors of some dipeptides (Leu–Leu, Gly–Leu, and Leu–Gly) focusing on the pH effects were investigated on Chirobiotic TM T and R [ 61 ]. Adsorption of Leu–Leu and Leu–Gly was found to rely on the ion–ion association between the solute and selector, which was controlled largely by the ionic forms of the solute and, to a smaller degree, by the ionization state of the selector.…”

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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“…Temperature dependence and thermodynamic study Asnin and co-workers have recently studied the enantioseparation of some dipeptides applying macrocyclic antibiotic-based CSPs and reported correlation between ∆H • , ∆S • or ∆G • and the pH or MeOH content of the mobile phase [21,22]. To characterize the employed systems from a thermodynamic point of view, the effect of temperature on the chromatographic parameters in the temperature range 10−50 • C (at 10 • C increments) was studied.…”

Section: 4mentioning

confidence: 99%

“…The difference in the change in standard enthalpy (Δ(Δ H° )) and entropy (Δ(Δ S° )) for the two enantiomers can be calculated on the basis of Eq. () [19–22],

\ln α = - \frac{Δ (Δ H^{\circ})}{R T} + \frac{Δ (Δ S^{\circ})}{R},

where R is the universal gas constant, T is temperature in Kelvin, and α is the apparent selectivity factor. All possibilities and problems of calculation of the thermodynamic parameters were excellently summarized by Asnin and Stepanova [20].…”

Section: Introductionmentioning

confidence: 99%

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Cinchona‐alkaloid‐based zwitterionic chiral stationary phases as potential tools for high‐performance liquid chromatographic enantioseparation of cationic compounds of pharmaceutical relevance

Tanács

Bajtai

Berkecz

et al. 2021

J of Separation Science

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Enantiomers of cationic compounds of pharmaceutical relevance, namely tetrahydro-ß-carboline and 1,2,3,4-tetrahydroisoquinoline analogs, were separated by high-performance liquid chromatography. Separations were performed on Cinchona-alkaloid-based zwitterionic ion exchanger type chiral stationary phases applied as cation exchangers using mixtures of methanol and acetonitrile or tetrahydrofuran as bulk solvent components containing triethylammonium acetate or ammonium acetate as organic salt additives. On the zwitterionic ZWIX(+) and ZWIX(−) columns investigated, retention and enantioseparation of the studied basic analytes were influenced by the nature and concentration of the organic components of the mobile phase. The effect of organic salt additives on the retention behavior of the studied analytes can be described by the stoichiometric displacement model related to the counterion concentration. Investigations on the structure-retention relationships were performed applying different mobile phase systems for the two types of cationic analytes. For the thermodynamic characterization, parameters such as changes in standard enthalpy (Δ(ΔH • )), entropy (Δ(ΔS • )), and free energy (Δ(ΔG • )) were calculated on the basis of van't Hoff plots derived from the ln α versus 1/T curves. In most cases, enthalpy-driven enantioseparations were observed, with a consistent dependence of the calculated thermodynamic parameters on the mobile phase composition. Elution sequences of the studied compounds were determined in all cases.

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Enantioselective retention mechanisms of dipeptides on antibiotic-based chiral stationary phases: Leucyl-leucine, glycyl-leucine, and leucyl-glycine as case studies

Cited by 15 publications

References 28 publications

Chiral separation of dipeptides on Cinchona‐based zwitterionic chiral stationary phases under buffer‐free reversed‐phase conditions

Chiral separation of dipeptides on Cinchona‐based zwitterionic chiral stationary phases under buffer‐free reversed‐phase conditions

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

Cinchona‐alkaloid‐based zwitterionic chiral stationary phases as potential tools for high‐performance liquid chromatographic enantioseparation of cationic compounds of pharmaceutical relevance

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