A1 Journal article (refereed)
Selective recognition of neutral guests in an aqueous medium by a biomimetic calix[6]cryptamide receptor (2016)

Lascaux, A., De Leener, G., Fusaro, L., Topic, F., Rissanen, K., Luhmer, M., & Jabin, I. (2016). Selective recognition of neutral guests in an aqueous medium by a biomimetic calix[6]cryptamide receptor. Organic and Biomolecular Chemistry, 14(2), 738-746. https://doi.org/10.1039/C5OB02067K

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Publication details

All authors or editors: Lascaux, Angélique; De Leener, Gaël; Fusaro, Luca; Topic, Filip; Rissanen, Kari; Luhmer, Michel; Jabin, Ivan

Journal or series: Organic and Biomolecular Chemistry

ISSN: 1477-0520

eISSN: 1477-0539

Publication year: 2016

Volume: 14

Issue number: 2

Pages range: 738-746

Publisher: RSC Publications

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/C5OB02067K

Publication open access: Not open

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The design of artificial receptors that can efficiently work in water is a challenging research area. A possible biomimetic approach for the elaboration of such receptors consists of associating a hydrophobic cavity with a polar polyfunctional binding site. On this basis, a hydrophilic calix[6]cryptamide decorated with oligo(ethylene glycol) units (i.e.8) was synthesized through an efficient [1 + 1] macrocyclization reaction as the key-step. The complexation of neutral molecules was evaluated by NMR spectroscopy through competition experiments either in apolar or aqueous media. In both media, host 8 can bind neutral species that display H-bonding acceptor and donor groups such as amides or ureas. Interestingly, the most polar and acidic molecule is the best guest in chloroform and the worst one in an aqueous medium, highlighting the importance of the environment. As shown by NMR and X-ray diffraction data, the mode of recognition involves a complementary DAAAD-ADDDA quintuple H-bonding array between the binding partners as well as multiple CH–π interactions. A comparison of this calix[6]arene-based host–guest system with the binding site of biotin-binding proteins shows strong similarities. Besides, the acid–base control of the binding properties of receptor 8 in aqueous media is highly reminiscent of allosteric processes encountered in natural systems.

Free keywords: artificial receptors; biomimetics; aqueous medium

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Ministry reporting: Yes

Reporting Year: 2016

JUFO rating: 1

Last updated on 2021-18-06 at 18:51