Molecular dynamics simulations of the chiral recognition mechanism for a polysaccharide chiral stationary phase in enantiomeric chromatographic separations

Wang, Xiaoyu; House, David; Oroskar, Priyanka A.; Oroskar, Anil R.; Oroskar, Asha; Jameson, Cynthia J.; Murad, Sohail

doi:10.1080/00268976.2019.1647360

Cited by 26 publications

(34 citation statements)

References 90 publications

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“…Even though this study describes an interesting approach to design a model closer to a real system, the benefit of modelling the achiral support is not fully validated by the obtained results. Indeed, in some cases the modelled ADMPC/ silica slab setting produced similar results with respect to the modelled ADMPC alone [126].…”

Section: Intermolecular Noncovalent Interactions Underlying Enantiodimentioning

confidence: 63%

“…In a different situation, recently, the same authors observed that π-π interaction can positively cooperate with HB formation [126]. A 12-mer ADMPC, weakly restrained, was used to model the enantiosepation of 6 on ADMPC (EEO experimental = R-S) by using heptane/2-propanol as explicit solvent, with 100 ns as MD production time (Fig.…”

Section: Intermolecular Noncovalent Interactions Underlying Enantiodimentioning

confidence: 99%

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Noncovalent interactions in high-performance liquid chromatography enantioseparations on polysaccharide-based chiral selectors

Peluso

Mamane

Dallocchio

et al. 2020

Journal of Chromatography A

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HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

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Section: Intermolecular Noncovalent Interactions Underlying Enantiodimentioning

confidence: 63%

Section: Intermolecular Noncovalent Interactions Underlying Enantiodimentioning

confidence: 99%

Noncovalent interactions in high-performance liquid chromatography enantioseparations on polysaccharide-based chiral selectors

Peluso

Mamane

Dallocchio

et al. 2020

Journal of Chromatography A

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“…For acetonitrile molecule, widely used, [55] the general amber force field (GAFF) was employed. [56] The systems considered in this study were described in Table S1 in Data S3.…”

Section: Models and Simulation Methodsmentioning

confidence: 99%

Nanostructures from protected L/L and D/L amino acid containing dipeptides

et al. 2020

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The self-assembly of N-and C-protected alternating L/L and D/L amino acids containing dipeptides, Boc-L-Val-L-Ile-OMe (1), Boc-D-Val-L-Ile-OMe (2), Boc-L-Ile-L-Val-OMe (3), and Boc-L-Ile-D-Val-OMe (4) has been investigated. Field emission scanning electron microscopy (FESEM) and atomic force microscopy (AFM) images indicated that 1 and 3 self-associated to form highly organized straight net microrods, whereas 2 and 4 self-assembled to form hexagonal hollow microtube-like architecture in the acetonitrile-water medium. To understand the physical basis of such differential behavior, we performed X-ray diffraction pattern analyses. The singlecrystal X-ray diffraction (SC-XRD) study revealed that 1 and 2 self-assembled to form slightly different helix-like architectures. The higher-order association of 2 exhibited a hollow hexagonal tube-like superstructure. The thermal stability of the nanostructures also varied based on the chiroptical composition of the dipeptides. Experimental findings were corroborated well with computational studies. The obtained results may be helpful in nano-biotechnology as well as in material science.

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“…Particularly for the polysaccharide-based CSPs, we have used MD simulations to provide a molecular level understanding of the dynamic separation process and, for a given set of conditions, for predicting which enantiomer elutes first, and for an estimate of the ratio of residence times or separation factor. [29][30][31] Some questions that can be answered by MD simulations are:…”

Section: Simulations Provide a Dynamic Atomistic Representation Ofmentioning

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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Molecular dynamics simulations of the chiral recognition mechanism for a polysaccharide chiral stationary phase in enantiomeric chromatographic separations

Cited by 26 publications

References 90 publications

Noncovalent interactions in high-performance liquid chromatography enantioseparations on polysaccharide-based chiral selectors

Noncovalent interactions in high-performance liquid chromatography enantioseparations on polysaccharide-based chiral selectors

Nanostructures from protected L/L and D/L amino acid containing dipeptides

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

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