Enantioseparation of new triadimenol antifungal active compounds by electrokinetic chromatography and molecular modeling study of chiral recognition mechanisms

Abstract

Chiral separation of 12 new triadimenol antifungal active compounds by electrokinetic chromatography and chiral recognition mechanisms by computer-aided molecular modeling techniques were studied. Seven neutral cyclodextrins were used as chiral selectors. Heptakis-(2,3,6-tri-O-methyl)-β-cyclodextrin (TM-β-CD) exhibited a very high enantioselectivity power to 12 active compounds compared to the other tested CDs. The influences of the concentration of TM-β-CD, buffer pH, buffer concentration, applied voltage, and temperature were investigated, respectively. Under the optimum separation conditions, all the 12 active compounds were baseline separated and the resolutions of most compounds were beyond 2.50. The study of the analyte structure-enantioseparation relationships showed that substitutions in the side chains played important roles on enantiomeric separation. By means of computer-aided molecular modeling software Discovery Studio 2.5/Sybyl 7.0/Gold 3.0.1, inclusion process between TM-β-CD and these enantiomers was investigated and their binding energies were calculated. The results suggested that the enantioseparation result related to the difference in binding energy. And the good separation obtained in the presence of the TM-β-CD chiral selector was due to the big binding energy difference of two enantiomers with the chiral selector.

Enantioresolution in electrokinetic chromatography-complete filling technique using sulfated gamma-cyclodextrin. Software-free topological anticipation

“…The approaches used in this field are mainly nuclear magnetic resonance (NMR) spectroscopy [9][10][11], molecular modelling [12][13][14], and computer simulations [8]. The combination of chiral CE with molecular modelling and NMR experiments or other supporting techniques (e.g.…”

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

“…Chai and co‐authors reported the enantioseparation of triadimenol antifungal compounds by CEKC with TM‐β‐CD, which showed higher enantiorecognition ability compared to other CDs such as α‐CDs, HP‐α‐CD, hydroxypropy‐β‐CD (HP‐β‐CD), and 2,6‐DM‐β‐CD [182]. In this study, molecular docking was used to visualized the structures of low‐energy guest/TM‐β‐CD complexes and the involved noncovalent interactions.…”

Chiral Separations by Capillary Electrophoresis and related Techniques with Different Chiral Selectors: A Review

“…In addition, the plurality of CD derivatives across the spaces and substituents meets the possibility of enantiomeric separation for large-scale chiral compounds [152]. CDs act as chiral selectors to separate enantiomers and are suitable for related strategies, such as capillary derivatization, inclusion complex formation mec-hanism, chiral recognition, molecular modeling, quantitative approaches, also detection of analytes [153][154][155][156][157][158][159][160][161][162][163]. 15 different cyclodextrin derivatives were investigated as a chiral complexing reagent.…”