Publication: Molecular dynamics simulations of chiral recognition for the Whelk-O1 chiral stationary phase

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Title	Molecular dynamics simulations of chiral recognition for the Whelk-O1 chiral stationary phase
Authors/Editors*	C. F. Zhao and N. M. Cann
Where published*	Analytical Chemistry
How published*	Journal
Year*	2008
Volume	(in press)
Number
Pages	13 page proof
Publisher
Keywords	Molecular Dynamics Simulation, Whelk-O1, Chiral Stationary Phase, HPLC, Chiral Recognition, Separation Mechanism, Three Point Interaction Model
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Abstract	In this article, we examine the docking of ten analytes on the Whelk-O1 stationary phase. A proper representation 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 which is often dominant and analyze the conditions that lead to alternate docking modes.