Poly-proline-based chiral stationary phases: A molecular dynamics study of triproline, tetraproline, pentaproline and hexaproline interfaces

Ashtari, M.; Cann, N. M.

doi:10.1016/j.chroma.2012.09.075

Cited by 14 publications

(14 citation statements)

References 61 publications

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“…This was attributed to a conformational CS disorder promoted in such conditions [7]. The observation reinforces with chemical evidence the theoretical results obtained by Cann and co-workers [11,12]. Using molecular dynamics calculations, these authors concluded that protic solvents alter the distribution of conformational populations for polyproline CSs by establishing H-bonding.…”

Section: Introductionsupporting

confidence: 86%

Effects of supercritical fluid chromatography conditions on enantioselectivity and performance of polyproline-derived chiral stationary phases

Novell

Méndez²,

Minguillón

2015

Journal of Chromatography A

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Section: Introductionsupporting

confidence: 86%

Effects of supercritical fluid chromatography conditions on enantioselectivity and performance of polyproline-derived chiral stationary phases

Novell

Méndez²,

Minguillón

2015

Journal of Chromatography A

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“…Cann et al have also carried out MD simulations of chiral separations on proline-based CSPs. 40,41,55,56 An example of their simulation box is shown in Figure 1 with the TMA-(Pro)6-N(CH3)-tether CSP interacting with the enantiomers of α-methyl-9-anthracenemethanol in the presence of a n-hexane/2-propanol solvent. 41 In the latter study, they find that having tert-butyl end groups with an ether linkage rather than directly attached to the C O of the diproline chiral selectors made a difference in the accessibility of the analyte to the selector, that is, more accessible when the configuration is more extended via H-bonding to the solvent, more pronounced in 70/30 water/methanol than in 70/30 n-hexane/2-propanol.…”

Section: Simulations Of Chiral Analytes On Prolinetype Selectorsmentioning

confidence: 99%

Molecular dynamics simulations of enantiomeric separations as an interfacial process in HPLC

2021

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Since chromatographic separation is a dynamic process, with the interactions between the drug and the chiral stationary phase mediated by the solvent, no single interacting structure, such as could be found by minimizing the energy, could possibly describe and account for the ratio of residence times in the chromatographic column for the enantiomeric pair. We describe the use of explicit-solvent fully atomistic molecular dynamics simulations, permitting all the interactions between the atoms constituting the chiral stationary phase, solvent molecules and the drug molecule. This allows us to better understand the molecular dynamic chiral recognition that provides the discrimination, which results in the separation of enantiomers by high performance liquid chromatography. It also provides a means of predicting, for a given set of conditions, which enantiomer elutes first and an estimate of the expected separation factor. In this review, we consider the use of molecular dynamics toward this understanding and prediction.

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“…Interestingly, Gasparrini and co‐workers developed a general scheme based on a systematic and automatic “quasi‐flexible” docking approach for studying stereoselective recognition mechanisms, validating it on a leucine‐containing Pirkle‐type selector . Following previous theoretical studies involving proline‐based selector interfaces , recently Cann and Ashtari employed MD simulations (35‐40 ns of simulation time) to model the enantioseparation of six closely related aromatic analytes 1 ‐ 6 on four polyproline‐based CSPs I ‐ IV (Fig. ) .…”

Section: Donor‐acceptor Chiral Selectorsmentioning

confidence: 99%

Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

et al. 2019

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Liquid‐phase enantioseparations have been fruitfully applied in several fields of science. Various applications along with technical and theoretical advancements contributed to increase significantly the knowledge in this area. Nowadays, chromatographic techniques, in particular HPLC on chiral stationary phase, are considered as mature technologies. In the last thirty years, CE has been also recognized as one of the most versatile technique for analytical scale separation of enantiomers. Despite the huge number of papers published in these fields, understanding mechanistic details of the stereoselective interaction between selector and selectand is still an open issue, in particular for high‐molecular weight chiral selectors like polysaccharide derivatives. With the ever growing improvement of computer facilities, hardware and software, computational techniques have become a basic tool in enantioseparation science. In this field, molecular docking and dynamics simulations proved to be extremely adaptable to model and visualize at molecular level the spatial proximity of interacting molecules in order to predict retention, selectivity, enantiomer elution order, and profile noncovalent interaction patterns underlying the recognition process. On this basis, topics and trends in using docking and molecular dynamics as theoretical complement of experimental LC and CE chiral separations are described herein. The basic concepts of these computational strategies and seminal studies performed over time are presented, with a specific focus on literature published between 2015 and November 2018. A systematic compilation of all published literature has not been attempted.

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Poly-proline-based chiral stationary phases: A molecular dynamics study of triproline, tetraproline, pentaproline and hexaproline interfaces

Cited by 14 publications

References 61 publications

Effects of supercritical fluid chromatography conditions on enantioselectivity and performance of polyproline-derived chiral stationary phases

Effects of supercritical fluid chromatography conditions on enantioselectivity and performance of polyproline-derived chiral stationary phases

Molecular dynamics simulations of enantiomeric separations as an interfacial process in HPLC

Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

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