Enantioselective retention mechanisms of dipeptides on antibiotic-based chiral stationary phases. II. Effect of the methanol content in the mobile phase

Kopchenova, Margarita V.; Vozisov, Stepan E.; Klochkova, Mariya A.; Klimova, Yana A.

doi:10.1016/j.chroma.2020.461371

Cited by 17 publications

(4 citation statements)

References 27 publications

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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 ]. The lipophilicity of the dipeptides was found to be a determining parameter in the description of their retention behavior, strongly affected by the MeOH content of the mobile phase.…”

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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“…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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Electrochemical chiral sensor for levofloxacin detection base on Cu/Fe-BTC amplification

Deng,

Li,

et al. 2023

Microchim Acta

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Enantioselective retention mechanisms of dipeptides on antibiotic-based chiral stationary phases. II. Effect of the methanol content in the mobile phase

Cited by 17 publications

References 27 publications

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

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

Electrochemical chiral sensor for levofloxacin detection base on Cu/Fe-BTC amplification

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