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

Varfaj, Ina; Pershina, Margarita V.; Stepanova, Maria V.; Sardella, Roccaldo; Carotti, Andrea

doi:10.1016/j.chroma.2022.463158

Cited by 4 publications

(5 citation statements)

References 24 publications

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“…Cyclodextrin (CD) and its derivatives are widely used for their ability to form inclusion complexes through host‐guest non‐covalent interactions. For calculating the interaction, molecular docking and molecular dynamics are two of the most used simulations 42–49 . In most cases, the complexes formed by various guest molecules with CDs are amorphous, 39 so they are highly disordered and dynamic.…”

Section: Resultsmentioning

confidence: 99%

“…For calculating the interaction, molecular docking and molecular dynamics are two of the most used simulations. [42][43][44][45][46][47][48][49] In most cases, the complexes formed by various guest molecules with CDs are amorphous, 39 so they are highly disordered and dynamic. In the inclusion complexes, the guests exist in various conformations and in various poses.…”

Section: Molecular Simulation and Mechanismmentioning

confidence: 99%

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Novel ethylenediamine‐β‐cyclodextrin grafted membranes for the chiral separation of mandelic acid and its derivatives

Zhou,

Wei,

et al. 2024

Chirality

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In the present study, flat cellulose acetate ultrafiltration membranes were prepared first by nonsolvent induced phase separation method. Then chiral membranes for separating the enantiomers were prepared by grafting the ultrafiltration membranes using ethylenediamine‐β‐cyclodextrin as the chiral selector and epichlorohydrin as the spacer arm. The pure water permeability of the ultrafiltration membrane was around 115 L·m−2·h−1·bar−1. The properties of the chiral membranes were characterized using infrared spectroscopy (ATR‐FTIR), X‐ray photoelectron spectroscopy (XPS), and scanning electron microscopy (SEM). The chiral membrane performance in enantiomer separation was evaluated with racemates, such as mandelic acid (MA), 2‐chloromandelic acid (2‐ClMA), 4‐chloromandelic acid (4‐ClMA), and methyl mandelate (MM). The influence of feed concentration on the separation efficiency was also investigated. The results indicated that the enantiomeric excess percentages (e.e%) of the racemic mixtures for these four chiral compounds were up to 31.8%, 25.4%, 17.8%, and 32.6%, respectively. The binding free energy of the chiral selector with the (S)‐enantiomer calculated by molecular dynamics simulations was stronger than that with the (R)‐enantiomer, which was consistent with the experimental results (higher concentration of (R)‐enantiomer in the permeate). This supports the affinity absorption‐separation mechanism.

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Section: Resultsmentioning

confidence: 99%

Section: Molecular Simulation and Mechanismmentioning

confidence: 99%

Novel ethylenediamine‐β‐cyclodextrin grafted membranes for the chiral separation of mandelic acid and its derivatives

Zhou,

Wei,

et al. 2024

Chirality

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show abstract

“…Furthermore, the binding positions to the selector differed for the enantiomers. The group of Carotti also evaluated the chiral interaction between the enantiomers of the dipeptides Ala-Ala, Gly-Leu, Leu-Gly, and Leu-Leu and ristocetin A as chiral selectors simultaneously considering two alternative binding modes of the selector to a solid support [139]. Ristocetin A can be linked to silica gel via one of the two amino functions of the molecule, one of them present in the carbohydrate vancosamine (termed linkage A) and the other one in the 3,4-dihydroxyphenylalanine moiety in the macrocycle (termed linkage B).…”

Section: Macrocyclic Antibioticsmentioning

confidence: 99%

“…Chemical structures (left) and molecular modeling structures (right) of ristocetin A linked to silica gel via the amino groups in the vincosamine moiety (linkage A, top) or in the 3,4‐dihydroxyphenylalanine moiety (linkage B, bottom). (Reproduced with permission [139], © by Elsevier 2022).…”

Section: Chiral Selectorsmentioning

confidence: 99%

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Update on chiral recognition mechanisms in separation science

Scriba

2024

J of Separation Science

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The stereospecific analysis of chiral molecules is an important issue in many scientific fields. In separation sciences, this is achieved via the formation of transient diastereomeric complexes between a chiral selector and the selectand enantiomers driven by molecular interactions including electrostatic, ion‐dipole, dipole‐dipole, van der Waals or π‐π interactions as well as hydrogen or halogen bonds depending on the nature of selector and selectand. Nuclear magnetic resonance spectroscopy and molecular modeling methods are currently the most frequently applied techniques to understand the selector‐selectand interactions at a molecular level and to draw conclusions on the chiral separation mechanism. The present short review summarizes some of the recent achievements for the understanding of the chiral recognition of the most important chiral selectors combining separation techniques with molecular modeling and/or spectroscopic techniques dating between 2020 and early 2024. The selectors include polysaccharide derivatives, cyclodextrins, macrocyclic glycopeptides, proteins, donor‐acceptor type selectors, ion‐exchangers, crown ethers, and molecular micelles. The application of chiral ionic liquids and chiral deep eutectic solvents, as well as further selectors, are also briefly addressed. A compilation of all published literature on chiral selectors has not been attempted.

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A journey in unraveling the enantiorecognition mechanism of 3,5-dinitrobenzoyl-amino acids with two Cinchona alkaloid-based chiral stationary phases: The power of molecular dynamic simulations

Varfaj,

Labikova,

Sardella

et al. 2024

Analytica Chimica Acta

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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

Cited by 4 publications

References 24 publications

Novel ethylenediamine‐β‐cyclodextrin grafted membranes for the chiral separation of mandelic acid and its derivatives

Novel ethylenediamine‐β‐cyclodextrin grafted membranes for the chiral separation of mandelic acid and its derivatives

Update on chiral recognition mechanisms in separation science

A journey in unraveling the enantiorecognition mechanism of 3,5-dinitrobenzoyl-amino acids with two Cinchona alkaloid-based chiral stationary phases: The power of molecular dynamic simulations

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