Terpenes Show Nanomolar Affinity and Selective Binding with Cucurbit[8]uril

Miguel A. Romero; José A. González-Delgado; Johan Mendoza; Jesús F. Arteaga; Nuno Basílio; Uwe Pischel

doi:10.1002/ijch.201700119

Terpenes Show Nanomolar Affinity and Selective Binding with Cucurbit[8]uril

Miguel A. Romero, José A. González-Delgado, Johan Mendoza, Jesús F. Arteaga, Nuno Basílio, Uwe Pischel

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

Eucalyptol, fenchyl alcohol, and geranylamine were tested for the binding to cucurbit[8]uril. Nanomolar affinities were found, giving rise to a highly selective binding of the terpenes by cucurbit[8]uril when compared to the smaller cucurbit[7]uril. This was rationalized with a better size fit with the larger macrocycle. These notions were supported by the calculation of the packing coefficient and NMR measurements of the free and complexed terpenes. The binding process is mainly enthalpically driven, which is associated with the release of high-energy water.

Original language	English
Pages (from-to)	487-492
Number of pages	6
Journal	Israel Journal of Chemistry
Volume	58
Issue number	3
DOIs	https://doi.org/10.1002/ijch.201700119
Publication status	Published - 1 Apr 2018

Keywords

competitive displacement
cucurbiturils
differential binding
host-guest systems
terpene

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10.1002/ijch.201700119

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abstract = "Eucalyptol, fenchyl alcohol, and geranylamine were tested for the binding to cucurbit[8]uril. Nanomolar affinities were found, giving rise to a highly selective binding of the terpenes by cucurbit[8]uril when compared to the smaller cucurbit[7]uril. This was rationalized with a better size fit with the larger macrocycle. These notions were supported by the calculation of the packing coefficient and NMR measurements of the free and complexed terpenes. The binding process is mainly enthalpically driven, which is associated with the release of high-energy water.",

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AU - Basílio, Nuno

AU - Pischel, Uwe

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Terpenes Show Nanomolar Affinity and Selective Binding with Cucurbit[8]uril

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Keywords

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