Mass transfer kinetics on modern Whelk-O1 chiral stationary phases made on fully- and superficially-porous particles

Felletti, Simona; Catani, Martina; Mazzoccanti, Giulia; Luca, Chiara De; Lievore, Giulio; Buratti, Alessandro; Pasti, Luisa; Gasparrini, Francesco; Cavazzini, Alberto

doi:10.1016/j.chroma.2020.461854

Cited by 19 publications

(16 citation statements)

References 41 publications

(67 reference statements)

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“…Indeed, it is in the stationary phase where the enantiomers will spend different times, due to the formation of transient diastereoismers with different energy. The same finding about localized adsorption in chiral chromatography, when the enantiomers are characterized by the same longitudinal diffusion, was achieved in ref through a more mathematical approach.…”

Section: Resultssupporting

confidence: 64%

Understanding the Transition from High-Selective to High-Efficient Chiral Separations by Changing the Organic Modifier with Zwitterionic-Teicoplanin Chiral Stationary Phase

et al. 2023

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The retention behavior of small molecules and N-protected amino acids on a zwitterionic teicoplanin chiral stationary phase (CSP), prepared on superficially porous particles (SPPs) of 2.0 μm particle diameter, has shown that efficiency and enantioselectivity, and so enantioresolution, dramatically change depending on the employed organic modifier. In particular, it was found that while methanol permits the boost of enantioselectivity and resolution of the amino acids, at the cost of efficiency, acetonitrile allows for the ability to reach extraordinary efficiency even at high flow rates (with reduced plate height <2 and up to 300,000 plates/m at the optimum flow rate). To understand these features, an approach based on the investigation of mass transfer through the CSP, the estimation of the binding constants of amino acids on the CSP, and the assessment of compositional properties of the interfacial region between bulk mobile phase and solid surface has been adopted.

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Section: Resultssupporting

confidence: 64%

Understanding the Transition from High-Selective to High-Efficient Chiral Separations by Changing the Organic Modifier with Zwitterionic-Teicoplanin Chiral Stationary Phase

et al. 2023

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“…1365 A similar approach was reported for the enantioseparation of 1indanol using inverse method in order to derive adsorption isotherms 1366 as well as to study the effect of the column dimension. 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.…”

Section: Nuclear Magnetic Resonancementioning

confidence: 99%

“…Another fundamental point is to find a correlation between kinetic and thermodynamic parameters by combining mass transfer investigation and adsorption isotherm determination. 1373…”

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%

“…First, it will be very important to understand how C ads depends on some experimental variables such as the MP composition, the temperature, and the CS loading. Another fundamental point is to find a correlation between kinetic and thermodynamic parameters by combining mass transfer investigation and adsorption isotherm determination …”

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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Novel insights into the dependence of adsorption-desorption kinetics on particle geometry in chiral chromatography

De Luca,

Compagnin,

Nosengo

et al. 2024

Anal Bioanal Chem

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The existence of slow adsorption-desorption kinetics in chiral liquid chromatography is common knowledge. This may significantly contribute to worsening the efficiency and kinetic performance of a chromatographic run, especially when high flow rates are employed. Many attempts and protocols have been proposed to access this term, the so-called $$c_{ads}$$ c ads , but they are based on different (theoretical) assumptions. As a consequence, no official method is available for the estimation of the adsorption-desorption kinetics term. In this work, a novel approach to access $$c_{ads}$$ c ads is presented. This procedure combines experimental results obtained with kinetic and thermodynamic measurements. The investigations have been performed on two zwitterionic teicoplanin chiral stationary phases (CSPs) based on 1.9 $$\mu $$ μ m fully porous and 2.0 $$\mu $$ μ m superficially porous particles (FPPs and SPPs), using Z-D,L-Methionine as probe molecule. Kinetic studies have been performed through the combination of both stop-flow and dynamic measurements, while adsorption isotherms have been calculated through Inverse Method. This study has confirmed that, on both particle formats, analyte diffusion on the surface of the particle is negligible, meaning that adsorption is localized, and it has been demonstrated that adsorption-desorption kinetics is strongly dependent on particle geometry and, in particular, on the loading of chiral selector. These findings are fundamental not only to unravel novel aspects of the complex enantiorecognition mechanism but also to optimize the employment of CSPs for ultra-fast and preparative applications. Graphical abstract

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Mass transfer kinetics on modern Whelk-O1 chiral stationary phases made on fully- and superficially-porous particles

Cited by 19 publications

References 41 publications

Understanding the Transition from High-Selective to High-Efficient Chiral Separations by Changing the Organic Modifier with Zwitterionic-Teicoplanin Chiral Stationary Phase

Understanding the Transition from High-Selective to High-Efficient Chiral Separations by Changing the Organic Modifier with Zwitterionic-Teicoplanin Chiral Stationary Phase

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

Novel insights into the dependence of adsorption-desorption kinetics on particle geometry in chiral chromatography

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