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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), pp. 2717-2728. (doi:10.1002/chem.200601289).

Record type: Article

Abstract

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.

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More information

Published date: 2007
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

Identifiers

Local EPrints ID: 54372
URI: http://eprints.soton.ac.uk/id/eprint/54372
ISSN: 0947-6539
PURE UUID: 9e00967b-b318-430d-948e-d3b147694eda
ORCID for M.E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 31 Jul 2008
Last modified: 17 Jul 2017 14:35

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Contributors

Author: A. Ragusa
Author: J.M. Hayes
Author: M.E. Light ORCID iD
Author: J.D. Kilburn

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