Molecular Dynamics Study of Chiral Recognition for the Whelk-O1 Chiral Stationary Phase
In this article, we examine the docking of 10 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 represen...
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| Veröffentlicht in: | Analytical chemistry (Washington) 2008-04, Vol.80 (7), p.2426-2438 |
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| creator | Zhao, C. F Cann, N. M |
| description | In this article, we examine the docking of 10 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 that is often dominant and analyze the conditions that lead to alternate docking modes. |
| doi_str_mv | 10.1021/ac702126y |
| format | Article |
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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.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18321129</pmid><doi>10.1021/ac702126y</doi><tpages>13</tpages></addata></record> |
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| subjects | Analytical chemistry Chemistry Chromatography, High Pressure Liquid - instrumentation Chromatography, High Pressure Liquid - methods Computer Simulation Exact sciences and technology General, instrumentation Hydrogen Hydrogen Bonding Hydrogen bonds Models, Molecular Molecular biology Molecular Conformation Molecules Probability Stereoisomerism |
| title | Molecular Dynamics Study of Chiral Recognition for the Whelk-O1 Chiral Stationary Phase |
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