Comparative study of complexation between cyclodextrins and xylazine using 1H NMR and molecular modelling methods

Ali, Sk Ajim; Muzaffar, Sughra; Imtiaz, Shah

doi:10.1016/j.molstruc.2019.06.080

Cited by 7 publications

(2 citation statements)

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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%