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New mathematic model for predicting chiral separation using molecular docking: Mechanism of chiral recognition of triadimenol analogues
Author(s) -
Zhang Guoqing,
Sun Qingyan,
Hou Ying,
Hong Zhanying,
Zhang Jun,
Zhao Liang,
Zhang Hai,
Chai Yifeng
Publication year - 2009
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.200900012
Subject(s) - enantiomer , docking (animal) , chemistry , hydrogen bond , phosphoric acid , molecular model , interaction energy , computational chemistry , chiral resolution , hydrophobic effect , combinatorial chemistry , stereochemistry , chromatography , molecule , organic chemistry , medicine , nursing
The purpose of this paper was to study the enantioseparation mechanism of triadimenol compounds by carboxymethylated (CM)‐β‐CD mediated CE. All the enantiomers were separated under the same experimental conditions to study the chiral recognition mechanism using a 30 mM sodium dihydrogen phosphate buffer at pH 2.2 adjusted by phosphoric acid. The inclusion courses between CM‐β‐CD and enantiomers were investigated by the means of molecular docking technique. It was found that there were at least three points (one hydrophobic bond and two hydrogen bonds) involved in the interaction of each enantiomer with the chiral selectors. A new mathematic model has been built up based on the results of molecular mechanics calculations, which could analyze the relationship between the resolution of enantioseparation and the interaction energy in the docking area. Comparing the results of the separation by CE, the established mathematic model demonstrated good capability to predict chiral separation of triadimenol enantiomers using CM‐β‐CD mediated CE.