Theoretical study on chiral recognition mechanism of ethyl-3-hydroxybutyrate with permethylated β-cyclodextrin

Shi, Jie‐Hua; Hu, Ying; Ding, Zuo-jing

doi:10.1016/j.comptc.2011.07.001

Cited by 15 publications

(5 citation statements)

References 38 publications

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“…As mentioned in the assay of thermodynamic parameters, the interaction between enantiomers and chiral selector, HP‐β‐CD plays a significant role in the process of chiral separation. The research on the chiral resolution mechanism of enantiomers on CD and its derivatives has aroused great attention 32–36 . To clarify the chiral resolution mechanism of ( R / S )‐MA, ( R / S )‐MMA, and ( R /S)‐PMA on HP‐β‐CD, the inclusion of HP‐β‐CD with each optical isomer was explored with help of molecular docking and MD approaches.…”

Section: Resultsmentioning

confidence: 99%

“…The research on the chiral resolution mechanism of enantiomers on CD and its derivatives has aroused great attention. [32][33][34][35][36] To clarify the chiral resolution mechanism of (R/S)-MA, (R/S)-MMA, and (R/S)-PMA on HPβ-CD, the inclusion of HP-β-CD with each optical isomer was explored with help of molecular docking and MD approaches. First, the inclusion between HP-β-CD and each optical isomer was imitated using semiflexible docking, and thus, each enantiomer-HP-β-CD complex with the lowest binding energy was obtained.…”

Section: Molecular Simulationmentioning

confidence: 99%

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Enantioseparation of mandelic acid and substituted derivatives by high‐performance liquid chromatography with hydroxypropyl‐β‐cyclodextrin as chiral mobile additive and evaluation of inclusion complexes by molecular dynamics

et al. 2021

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The enantioseparation and resolution mechanism of mandelic acid (MA), 4-methoxymandelic acid (MMA), and 4-propoxymandelic acid (PMA) were investigated by reversed-phase high-performance liquid chromatography (HPLC) with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) as a chiral mobilephase additive and molecular dynamics simulation. The suitable chromatographic conditions for the enantioseparation of MA, MMA, and PMA were obtained. Under the selected chromatographic conditions, these enantiomers could achieve baseline separation. The results of thermodynamic parameter analysis revealed that the main driven forces for the enantioseparation of MA, MMA, and PMA could be van der Waals forces and hydrogen-bonding interactions and the chromatographic retention of these chiral compounds was an enthalpy-driven process. The results of the molecular simulation revealed that their chiral resolution mechanism on HP-β-CD was responsible for the formation of inclusion complexes of enantiomers with HP-β-CD with different conformations and binding energies. And the binding energy of HP-β-CD with (S)-isomer was larger than that with (R)-isomer, which is consistent with the experimental results of the first elution of (S)-isomer. Additionally, it is also confirmed that the interaction energies included the van der Waals energy (ΔE vdw ), electrostatic energy (ΔE elec ), polar solvation energy, and SASA energy (ΔE sasa ), and the separation factor (α) was closely connected with the disparity in the binding energies of optical isomers and HP-β-CD complexes. Meanwhile, from molecular dynamics simulation, it can be found that the Δ (ΔE binding ), (Δ(ΔE binding ) = ΔE binding,R À ΔE binding,S ) value was in order of MA-HP-β-CD complex > MMA-HP-β-CD complex > PMA-HP-β-CD complex, which was consistent with the order of Δ(ΔG) values obtained from van't Hoff plot. This indicated that the molecular dynamics simulation has predictive function for chiral resolution.

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Section: Resultsmentioning

confidence: 99%

Section: Molecular Simulationmentioning

confidence: 99%

Enantioseparation of mandelic acid and substituted derivatives by high‐performance liquid chromatography with hydroxypropyl‐β‐cyclodextrin as chiral mobile additive and evaluation of inclusion complexes by molecular dynamics

et al. 2021

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“…Further studies combining CE experiments with NMR and/or molecular modeling investigations of the CD–analyte complexes include the enantioseparations of bupivacaine with HDMS‐β‐CD and HDAS‐β‐CD , sibutramine by methylated β‐CD , sitagliptin by β‐CD , baclofen by β‐CD , imperanene by sulfobutylether‐γ‐CD and (2‐hydroxy)propyl‐β‐CD , bupivacaine by sulfobutylether‐β‐CD as well as phenylalkyl acids and dansyl amino acids by positively charged β‐CD derivatives . Although not in combination with CE experiments, molecular docking studies have been performed on the complexes of permethylated β‐CD with mandelic acid derivatives and ethyl‐3‐hydroxybutyrate .…”

Section: Investigation Of Analyte–selector Complex Structurementioning

confidence: 99%

Recent advances in electrodriven enantioseparations

Jáč

Scriba

2012

J of Separation Science

109

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Capillary electromigration techniques have developed into significant analytical separation tools especially for enantioseparations. While CE can be considered a mature technique as documented by its wide applications, CEC is still in a developmental state despite many research efforts. The success of stereospecific CE separation methods is due to the high specificity and flexibility of the technique as well as the availability of many types of chiral selectors. Thus, numerous methods have been developed for the analysis of chiral compounds in chemical, biochemical, pharmaceutical, environmental, and forensic sciences. However, most reported applications deal with pharmaceuticals. The search for new chiral selectors also continued despite the fact that most applications were performed using cyclodextrins. Furthermore, CE has been combined with spectroscopic and molecular modeling studies in attempts to understand the interactions between chiral selectors and analytes. The present review focuses on recent examples of mechanistic aspects of capillary enantioseparations with regard to mathematical modeling of enantioseparations, investigations of the analyte-complex structures as well as new chiral selectors and applications of chiral analyses by CE and CEC. It covers the literature published between January 2011 and August 2012.

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“…The most important point to know about the supramolecular systems (Komarov et al, 2011;Krishnamoorthy et al, 2011) at the interface is the orientational correlation about the order of monolayer. In the case of study of the inclusion complexes (Almeida et al, 2011;Boonyarattanakalin et al, 2011;Pan et al, 2011;Shi et al, 2011), we calculate the order parameter (Sr). This property is defined in terms of second-order Legendre polynomials and is the average of an angle made by a section of the polymer chain in a specified direction.…”

Section: Properties Polymeric Systems Calculations and Analysismentioning

confidence: 99%

Molecular Dynamics Simulation of Synthetic Polymers

Sandoval¹

2012

Molecular Dynamics - Studies of Synthetic and Biological Macromolecules

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Theoretical study on chiral recognition mechanism of ethyl-3-hydroxybutyrate with permethylated β-cyclodextrin

Cited by 15 publications

References 38 publications

Enantioseparation of mandelic acid and substituted derivatives by high‐performance liquid chromatography with hydroxypropyl‐β‐cyclodextrin as chiral mobile additive and evaluation of inclusion complexes by molecular dynamics

Enantioseparation of mandelic acid and substituted derivatives by high‐performance liquid chromatography with hydroxypropyl‐β‐cyclodextrin as chiral mobile additive and evaluation of inclusion complexes by molecular dynamics

Recent advances in electrodriven enantioseparations

Molecular Dynamics Simulation of Synthetic Polymers

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