TY - JOUR A1 - Durmaz, V. A1 - Weber, M. A1 - Becker, Roland T1 - How to simulate affinities for host-guest systems lacking binding mode information: application to the liquid chromatographic separation of hexabromocyclododecane stereoisomers T2 - Journal of molecular modeling N2 - A novel approach for the simulation of host.guest systems by systematically scanning the host moleculefs orientations within the guest cavity is presented along with a thermodynamic strategy for determining preferential binding modes and corresponding optimal interaction energies between host and guest molecules. By way of example, the elution order of hexabromocyclododecane stereoisomers from high performance liquid chromatography separation on a permethylated β-cyclcodextrin stationary phase has been computed using classical molecular dynamics simulations with the explicit solvents water and acetonitrile. Comparison of estimated with experimental separation data reveals remarkable squared coefficients of correlation with R2=0.87 and a very high correlation RLOO2 . 0:72 using the leaveone-out cross-validation method and water as solvent. In particular, the approach presented shapes up as very robust in terms of the evaluated time range under consideration, reflecting well thermodynamic equilibria. These and further observations correlating with experimental results suggest the suitability of the underlying force fields and our multi-mode approach for the estimation of relative binding affinities for host–guest systems with unknown binding modes. PB - Springer CY - Berlin; Heidelberg KW - Molecular simulation KW - Molecular dynamics KW - Binding affinity KW - Elution order KW - Beta-cyclodextrin PY - 2012 UR - https://opus4.kobv.de/opus4-bam/frontdoor/index/index/docId/26112 AN - OPUS4-26112 SN - 1610-2940 SN - 0948-5023 VL - 18 IS - 6 SP - 2399 EP - 2408 AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany