title: Interactions between pyrazole derived enantiomers and Chiralcel OJ: Prediction of enantiomer absolute configurations and elution order by molecular dynamics simulations.
abstract: The separation of enantiomers and confirmation of their absolute configurations is significant in the development of chiral drugs. The interactions between the enantiomers of chiral pyrazole derivative and polysaccharide-based chiral stationary phase cellulose tris(4-methylbenzoate) (Chiralcel OJ) in seven solvents and under different temperature were studied using molecular dynamics simulations. The results show that solvent effect has remarkable influence on the interactions. Structure analysis discloses that the different interactions between two isomers and chiral stationary phase are dependent on the nature of solvents, which may invert the elution order. The computational method in the present study can be used to predict the elution order and the absolute configurations of enantiomers in HPLC separations and therefore would be valuable in development of chiral drugs.
authors.affiliation: School of Biotechnology and Chemical Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China.
authors.forename: Guixiang
authors.initials: G
authors.lastname: Hu
authors.affiliation: School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK. Electronic address: m.huang@qub.ac.uk.
authors.forename: Meilan
authors.initials: M
authors.lastname: Huang
authors.affiliation: School of Biotechnology and Chemical Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China.
authors.forename: Chengcai
authors.initials: C
authors.lastname: Luo
authors.affiliation: Minsheng Group Shaoxing Pharmaceutical Co., Ltd., Shaoxing 312071, China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Wang
authors.affiliation: School of Biotechnology and Chemical Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, China.
authors.forename: Jian-Wei
authors.initials: JW
authors.lastname: Zou
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D002482:Cellulose / Q000031:analogs & derivatives* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D019295:Computational Biology; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001565:Benzoates; D011720:Pyrazoles; C090722:tris(4-methylbenzoate)cellulose; C031280:pyrazole; D002482:Cellulose; C009504:4-toluic acid
keywords: Elution order; Enantiomer; Interaction; Molecular dynamics (MD); Solvent effect