Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules
Identifieur interne : 000B61 ( Main/Exploration ); précédent : 000B60; suivant : 000B62Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules
Auteurs : David Coquire [France] ; Stphane Le Gac [France] ; Ulrich Darbostpresent Address Icbms Institut De Chimie Et Biochimie Molculaire Et Supramolculaire Umr-Cnrs Universit De Lyon Universit Claude Bernard Lyon Cpe Lyon Bd Du Novembre Villeurbanne Cedex France. [France] ; Olivier Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs-Cea-Ujf Rue Des Martyrs Grenoble Cedex France. [France] ; Ivan Jabin [France, Belgique] ; Olivia Reinaud [France]Source :
- Organic & Biomolecular Chemistry [ 1477-0520 ] ; 2009.
Abstract
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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DOI: 10.1039/b902456e
Affiliations:
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D. Roosevelt 50, CP160/06, B-1050 Brussels</wicri:regionArea><wicri:noRegion>B-1050 Brussels</wicri:noRegion></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Belgique</country></affiliation></author><author wicri:is="90%"><name sortKey="Reinaud, Olivia" sort="Reinaud, Olivia" uniqKey="Reinaud O" first="Olivia" last="Reinaud">Olivia Reinaud</name><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Universit Paris Descartes (Paris 5), 45 rue des Saints-Pres, 75006 Paris</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Paris</settlement></placeName></affiliation><affiliation wicri:level="1"><country wicri:rule="url">France</country></affiliation></author></analytic><monogr></monogr><series><title level="j">Organic & Biomolecular Chemistry</title><title level="j" type="abbrev">Org. Biomol. Chem.</title><idno type="ISSN">1477-0520</idno><idno type="eISSN">1477-0539</idno><imprint><publisher>The Royal Society of Chemistry.</publisher><date type="published" when="2009">2009</date><biblScope unit="volume"></biblScope><biblScope unit="issue">12</biblScope><biblScope unit="page" from="2485">2485</biblScope><biblScope unit="page" to="2500">2500</biblScope></imprint><idno type="ISSN">1477-0520</idno></series><idno type="istex">EABA382D532EB5EA33CD5C32B05A43E14B9ABC94</idno><idno type="DOI">10.1039/b902456e</idno><idno type="ms-id">b902456e</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1477-0520</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">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.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li><li>Île-de-France</li></region><settlement><li>Le Havre</li><li>Paris</li></settlement></list><tree><country name="France"><region name="Île-de-France"><name sortKey="Coquire, David" sort="Coquire, David" uniqKey="Coquire D" first="David" last="Coquire">David Coquire</name></region><name sortKey="Coquire, David" sort="Coquire, David" uniqKey="Coquire D" first="David" last="Coquire">David Coquire</name><name sortKey="Darbostpresent Address Icbms Institut De Chimie Et Biochimie Molculaire Et Supramolculaire Umr Cnrs Universit De Lyon Universit Claude Bernard Lyon Cpe Lyon Bd Du Novembre Villeurbanne Cedex France, Ulrich" sort="Darbostpresent Address Icbms Institut De Chimie Et Biochimie Molculaire Et Supramolculaire Umr Cnrs Universit De Lyon Universit Claude Bernard Lyon Cpe Lyon Bd Du Novembre Villeurbanne Cedex France, Ulrich" uniqKey="Darbostpresent Address Icbms Institut De Chimie Et Biochimie Molculaire Et Supramolculaire Umr Cnrs Universit De Lyon Universit Claude Bernard Lyon Cpe Lyon Bd Du Novembre Villeurbanne Cedex France U" first="Ulrich" last="Darbostpresent Address Icbms Institut De Chimie Et Biochimie Molculaire Et Supramolculaire Umr-Cnrs Universit De Lyon Universit Claude Bernard Lyon Cpe Lyon Bd Du Novembre Villeurbanne Cedex France.">Ulrich Darbostpresent Address Icbms Institut De Chimie Et Biochimie Molculaire Et Supramolculaire Umr-Cnrs Universit De Lyon Universit Claude Bernard Lyon Cpe Lyon Bd Du Novembre Villeurbanne Cedex France.</name><name sortKey="Jabin, Ivan" sort="Jabin, Ivan" uniqKey="Jabin I" first="Ivan" last="Jabin">Ivan Jabin</name><name sortKey="Le Gac, Stphane" sort="Le Gac, Stphane" uniqKey="Le Gac S" first="Stphane" last="Le Gac">Stphane Le Gac</name><name sortKey="Reinaud, Olivia" sort="Reinaud, Olivia" uniqKey="Reinaud O" first="Olivia" last="Reinaud">Olivia Reinaud</name><name sortKey="Reinaud, Olivia" sort="Reinaud, Olivia" uniqKey="Reinaud O" first="Olivia" last="Reinaud">Olivia Reinaud</name><name sortKey="Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs Cea Ujf Rue Des Martyrs Grenoble Cedex France, Olivier" sort="Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs Cea Ujf Rue Des Martyrs Grenoble Cedex France, Olivier" uniqKey="Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs Cea Ujf Rue Des Martyrs Grenoble Cedex France O" first="Olivier" last="Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs-Cea-Ujf Rue Des Martyrs Grenoble Cedex France.">Olivier Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs-Cea-Ujf Rue Des Martyrs Grenoble Cedex France.</name><name sortKey="Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs Cea Ujf Rue Des Martyrs Grenoble Cedex France, Olivier" sort="Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs Cea Ujf Rue Des Martyrs Grenoble Cedex France, Olivier" uniqKey="Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs Cea Ujf Rue Des Martyrs Grenoble Cedex France O" first="Olivier" last="Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs-Cea-Ujf Rue Des Martyrs Grenoble Cedex France.">Olivier Snquepresent Address Laboratoire De Chimie Et Biologie Des Mtaux Umr Cnrs-Cea-Ujf Rue Des Martyrs Grenoble Cedex France.</name></country><country name="Belgique"><noRegion><name sortKey="Jabin, Ivan" sort="Jabin, Ivan" uniqKey="Jabin I" first="Ivan" last="Jabin">Ivan Jabin</name></noRegion><name sortKey="Jabin, Ivan" sort="Jabin, Ivan" uniqKey="Jabin I" first="Ivan" last="Jabin">Ivan Jabin</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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