Publication: Molecular Dynamics Study of Chiral Recognition for the Whelk-O 1 Chiral Stationary Phase

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Title	Molecular Dynamics Study of Chiral Recognition for the Whelk-O 1 Chiral Stationary Phase
Authors/Editors*	C.F. Zhao, N.M. Cann
Where published*	Analytical Chemistry
How published*	Journal
Year*	2008
Volume	80
Number
Pages	2426-2438
Publisher
Keywords	Chiral separation, Molecular recognition, Molecular Dynamics Simulation, Whelk-O 1, Chiral HPLC
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Abstract	In this article, we examine the docking of 10 analytes on the Whelk-O1 stationary phase. A proper epresentation of analyte flexibility is essential in the docking analysis, and analyte force fields have been developed from a series of B3LYP calculations. Molecular dynamics simulations of a representative Whelk-O1 interface, in the presence of racemic analyte and solvent, form the basis of the analysis of chiral selectivity. The most probable docking arrangements are identified, the energy changes upon docking are evaluated, and separation factors are predicted. From comparisons between the analytes, the mechanism of chiral selectivity is divided into contributions from hydrogen bonding, ring-ring interactions,steric hindrance, and molecular flexibility. We find that both hydrogen bonding and ring-ring interactions are necessary to localize the analyte within the Whelk-O1 cleft region. We also identify one docking mechanism that is often dominant and analyze the conditions that lead to alternate docking modes.