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Correlation between conformational equilibria of free host and guest binding affinity in non-preorganized receptors

AuthorsCarrillo Fumero, Romen ; Morales, E. ; Martín, Víctor S.; Martín, Tomás
Issue Date28-May-2013
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 78: 7785-7795 (2013)
AbstractPositive cooperativity between host conformational equilibria and guest binding has been widely reported in protein receptors. However, reported examples of this kind of cooperativity in synthetic hosts are scarce and largely serendipitous, among other things because it is hard to envision systems which display this kind of cooperativity. In order to shed some light on the correlation between conformational equilibria of free host and guest binding, selected structural modifications have been performed over a family of nonpreorganized hosts in order to induce conformational changes and to analyze their effect on the binding affinity. The conformational effect was evaluated by a theoretical conformational search and correlated with the ability of the receptors. All data suggest that those receptors that display the best association constants are able to sample folded conformations analogous to the conformational requirements for the binding of the guests. On the contrary, for those receptors where folded conformers are scarce, then the association constant and enantioselectivity clearly drop.
Publisher version (URL)https://pubs.acs.org/doi/abs/10.1021/jo400683j
Identifiersdoi: 10.1021/jo400683j
issn: 0022-3263
e-issn: 1520-6904
Appears in Collections:(IPNA) Artículos
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