Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 7, Issue 12, Pages 2485-2500Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b902456e
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- CNRS, Ministere de la Recherche
- l'Agence Nationale pour la Recherche [ANR-05-BLAN-0003]
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The selective recognition of substrates or cofactors is a key feature of biological processes. It involves coordination bonds, hydrogen bonding, charge/charge and charge/dipole interactions. In this Perspective, we describe how the calix[6] arene core can be functionalized and shaped to act as a biomimetic molecular receptor. The strategy relies on the selective introduction of three amino arms on alternate phenolic positions. Upon metal ion binding or self-assembly via multiple ion-pairing and H-bonding, these amino arms are projected towards each other, thus closing the calixarene small rim. The resulting cone-shaped receptors act as molecular funnels displaying high affinities for a variety of neutral guests. Their hosting properties can be finely tuned by changing the small or the large rim or by allosteric effects. Induced-fit processes are also often observed as the cavity can expand for large guests or shrink for small ones. Hence, the different families of calix[6] arene-based receptors presented here highlight the importance of having a flexible and polarized hydrophobic structure to accommodate the guest.
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