A combined computational and experimental approach for the analysis of the enantioselective potential of a new macrocyclic receptor for N-protected alpha-amino acids
Ragusa, A., Hayes, J.M., Light, M.E. and Kilburn, J.D. (2007) A combined computational and experimental approach for the analysis of the enantioselective potential of a new macrocyclic receptor for N-protected alpha-amino acids. Chemistry-a European Journal, 13, (9), 2717-2728. (doi:10.1002/chem.200601289).
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A new macrocyclic receptor incorporating a thiourea moiety has been synthesised. Crystal structures of the macrocycle showed that the receptor has a rigid backbone but the thiourea moiety can orientate itself to bind to a DMSO solvent molecule. Force-field (MMFFs) calculations were performed to model the macrocycle and its binding properties with respect to N-protected amino acids, which were measured experimentally by NMR titration. Binding free energies were calculated by using the mode integration algorithm (MINTA) or free-energy perturbation (FEP). Excellent qualitative agreement with experiment was obtained. To further exploit the accuracy of the free-energy predictions for this system, the faster free-energy algorithm MINTA was used as a prediction tool to test the binding affinity of the macrocycle towards a series of several other amino acid derivatives, which speeded up considerably the screening process and reduced laboratory costs.
|Keywords:||dynamics simulations, conformational, stochastic dynamics, receptors, host-guest systems, , recognition, van-der-waals, binding free-energies, molecular-force field, molecular modeling,enantioselectivity, free-energy calculations, monte-carlo, mmff94, electrostatic parameters, , free-energies, molecular|
Q Science > QD Chemistry
|Divisions:||University Structure - Pre August 2011 > School of Chemistry
|Date Deposited:||31 Jul 2008|
|Last Modified:||27 Mar 2014 18:37|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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