Prediction of Chiral Discrimination by ¥â-Cyclodextrins Using Grid-based Monte Carlo Docking Simulations

Bulletin of the Korean chemical society

Hyungwoo Park¹  Dong Wook Kim¹  Karpjoo Jeong¹  Suntae Hwang¹  Youngjin Choi¹  Seunho Jung¹ 

关键词: Chiral discrimination;    Conformational rigidity;    Cyclodextrin;    Grid-based Monte Carlo docking;    Inclusion complex;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

An efficiency of Monte Carlo (MC) docking simulations was examined for the prediction of chiral discrimination by cyclodextrins. Docking simulations were performed with various computational parameters for the chiral discrimination of a series of 17 enantiomers by �?-cyclodextrin (�?-CD) or by 6-amino-6-deoxy-�?- cyclodextrin (am-�?-CD). A total of 30 sets of enantiomeric complexes were tested to find the optimal simulation parameters for accurate predictions. Rigid-body MC docking simulations gave more accurate predictions than flexible docking simulations. The accuracy was also affected by both the simulation temperature and the kind of force field. The prediction rate of chiral preference was improved by as much as 76.7% when rigid-body MC docking simulations were performed at low-temperatures (100 K) with a sugar22 parameter set in the CHARMM force field. Our approach for MC docking simulations suggested that the conformational rigidity of both the host and guest molecule, due to either the low-temperature or rigid-body docking condition, contributed greatly to the prediction of chiral discrimination.

【 授权许可】

Unknown