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Selective recognition of quaternary ammonium ions and zwitterions by using a biomimetic bis-calix[6]arene-based receptor

Bibliographic reference Moerkerke, Steven ; Malytskyi, Volodymyr ; Marcélis, Lionel ; Wouters, Johan ; Jabin, Ivan. Selective recognition of quaternary ammonium ions and zwitterions by using a biomimetic bis-calix[6]arene-based receptor. In: Organic & Biomolecular Chemistry, Vol. 15, p. 8967-8974 (2017)
Permanent URL http://hdl.handle.net/2078/192620
  1. Kosswig Kurt, Surfactants, 10.1002/14356007.a25_747
  2. Yajeya Javier, De La Fuente Antonio, Criado Jose M., Bajo Victoria, S�nchez-Riolobos Adela, Heredia Margarita, Muscarinic agonist carbachol depresses excitatory synaptic transmission in the rat basolateral amygdala in vitro, 10.1002/1098-2396(200011)38:2<151::aid-syn6>3.0.co;2-k
  3. Hanson A. D., Rathinasabapathi B., Rivoal J., Burnet M., Dillon M. O., Gage D. A., Osmoprotective compounds in the Plumbaginaceae: a natural experiment in metabolic engineering of stress tolerance., 10.1073/pnas.91.1.306
  4. McNeil Scott D., Nuccio Michael L., Hanson Andrew D., Betaines and Related Osmoprotectants. Targets for Metabolic Engineering of Stress Resistance, 10.1104/pp.120.4.945
  5. Späth Andreas, König Burkhard, Molecular recognition of organic ammonium-ions in solution using synthetic receptors, 10.3762/bjoc.6.32
  6. Salonen Laura M., Ellermann Manuel, Diederich François, Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures, 10.1002/anie.201007560
  7. Perez Camilo, Koshy Caroline, Yildiz Özkan, Ziegler Christine, Alternating-access mechanism in conformationally asymmetric trimers of the betaine transporter BetP, 10.1038/nature11403
  8. A. Dalla Cort and L.Mandolini, Calixarenes as hosts for quats, in Calixarenes in action, ed. L. Mandolini and R. Ungaro, Imperial College Press, 2000
  9. Gaeta Carmine, Troisi Francesco, Neri Placido, endo-Cavity Complexation and Through-the-Annulus Threading of Large Calixarenes Induced by Very Loose Alkylammonium Ion Pairs, 10.1021/ol100578z
  10. Arduini Arturo, Bussolati Rocco, Credi Alberto, Secchi Andrea, Silvi Serena, Semeraro Monica, Venturi Margherita, Toward Directionally Controlled Molecular Motions and Kinetic Intra- and Intermolecular Self-Sorting: Threading Processes of Nonsymmetric Wheel and Axle Components, 10.1021/ja404270c
  11. Biros Shannon M., Rebek, Jr. Julius, Structure and binding properties of water-soluble cavitands and capsules, 10.1039/b508530f
  12. Zhang Dawei, Martinez Alexandre, Dutasta Jean-Pierre, Emergence of Hemicryptophanes: From Synthesis to Applications for Recognition, Molecular Machines, and Supramolecular Catalysis, 10.1021/acs.chemrev.6b00847
  13. Xue Min, Yang Yong, Chi Xiaodong, Zhang Zibin, Huang Feihe, Pillararenes, A New Class of Macrocycles for Supramolecular Chemistry, 10.1021/ar2003418
  14. Mutihac Lucia, Lee Jae Hong, Kim Jong Seung, Vicens Jacques, Recognition of amino acids by functionalized calixarenes, 10.1039/c0cs00005a
  15. McConnell Anna J., Beer Paul D., Heteroditopic Receptors for Ion-Pair Recognition, 10.1002/anie.201107244
  16. Mateus Pedro, Delgado Rita, Brandão Paula, Félix Vítor, A polyoxapolyaza macrobicyclic receptor for the recognition of zwitterions, 10.1039/c2ob25725d
  17. Perraud Olivier, Robert Vincent, Martinez Alexandre, Dutasta Jean-Pierre, A Designed Cavity for Zwitterionic Species: Selective Recognition of Taurine in Aqueous Media, 10.1002/chem.201101522
  18. Perraud Olivier, Robert Vincent, Gornitzka Heinz, Martinez Alexandre, Dutasta Jean-Pierre, Combined Cation-π and Anion-π Interactions for Zwitterion Recognition, 10.1002/anie.201106934
  19. Cochrane James R., Schmitt Aline, Wille Uta, Hutton Craig A., Synthesis of cyclic peptide hemicryptophanes: enantioselective recognition of a chiral zwitterionic guest, 10.1039/c3cc44784g
  20. Zhang Dawei, Bousquet Benjamin, Mulatier Jean-Christophe, Pitrat Delphine, Jean Marion, Vanthuyne Nicolas, Guy Laure, Dutasta Jean-Pierre, Martinez Alexandre, Synthesis, Resolution, and Absolute Configuration of Chiral Tris(2-pyridylmethyl)amine-Based Hemicryptophane Molecular Cages, 10.1021/acs.joc.7b00559
  21. Douteau-Guével Nathalie, Coleman Anthony W., Morel Jean-Pierre, Morel-Desrosiers Nicole, Complexation of the basic amino acids lysine and arginine by three sulfonatocalix[n]arenes (n = 4, 6 and 8) in water: microcalorimetric determination of the Gibbs energies, enthalpies and entropies of complexation, 10.1039/a806855k
  22. López Carlos, Sanna Elena, Carreras Lucas, Vega Manel, Rotger Carmen, Costa Antoni, Molecular Recognition of Zwitterions: Enhanced Binding and Selective Recognition of Miltefosine by a Squaramide-Based Host, 10.1002/asia.201200881
  23. Ballester Pablo, Shivanyuk Alexander, Far Adel Rafai, Rebek Julius, A Synthetic Receptor for Choline and Carnitine, 10.1021/ja0282689
  24. Daze Kevin D., Ma Manuel C. F., Pineux Florent, Hof Fraser, Synthesis of New Trisulfonated Calix[4]arenes Functionalized at the Upper Rim, and Their Complexation with the Trimethyllysine Epigenetic Mark, 10.1021/ol300243b
  25. Schnatwinkel Bjoern, Rekharsky Mikhail V., Borovkov Victor V., Inoue Yoshihisa, Mattay Jochen, Pyrogallol[4]arenes as artificial receptors for l-carnitine, 10.1016/j.tetlet.2008.10.108
  26. Ménand Mickaël, Leroy Axel, Marrot Jérôme, Luhmer Michel, Jabin Ivan, Induced-Fit Encapsulation by a 1,3,5-Alternate Calix[6]arene, 10.1002/anie.200901722
  27. Coquière David, Le Gac Stéphane, Darbost Ulrich, Sénèque Olivier, Jabin Ivan, Reinaud Olivia, Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules, 10.1039/b902456e
  28. Darbost Ulrich, Giorgi Michel, Hucher Nicolas, Jabin * Ivan, Reinaud * Olivia, A Calix[6]arene Receptor Rigidified by a Self-assembled Triammonium Cap: X-ray and NMR Characterization of the Binding of Polar Neutral Guests, 10.1080/10610270412331337303
  29. Le Poul Nicolas, Le Mest Yves, Jabin Ivan, Reinaud Olivia, Supramolecular Modeling of Mono-copper Enzyme Active Sites with Calix[6]arene-based Funnel Complexes, 10.1021/acs.accounts.5b00152
  30. Zahim Sara, Wickramasinghe Lasantha A., Evano Gwilherm, Jabin Ivan, Schrock Richard R., Müller Peter, Calix[6]azacryptand Ligand with a Sterically Protected Tren-Based Coordination Site for Metal Ions, 10.1021/acs.orglett.6b00410
  31. Le Gac Stéphane, Ménand Mickaël, Jabin Ivan, Second Generation of Calix[6]aza-Cryptands: Synthesis of Heteroditopic Receptors for Organic Ion Pairs, 10.1021/ol8021726
  32. Lascaux Angélique, Le Gac Stéphane, Wouters Johan, Luhmer Michel, Jabin Ivan, An allosteric heteroditopic receptor for neutral guests and contact ion pairs with a remarkable selectivity for ammonium fluoride salts, 10.1039/c0ob00211a
  33. G. De Leener , S.Moerkerke, R.Lavendomme, O.Reinaud and I.Jabin, in Calixarenes and Beyond, ed. P. Neri, J. L. Sessler and M.-X. Wang, Springer, 2016, pp. 113–140
  34. Ménand Mickaël, Jabin Ivan, Acid-Base Controllable Recognition Properties of a Highly Versatile Calix[6]crypturea, 10.1002/chem.200902792
  35. Cornut Damien, Marrot Jérôme, Wouters Johan, Jabin Ivan, Acid–base modulation of a versatile heteroditopic calix[6]arene based receptor, 10.1039/c1ob05759f
  36. Hamon Mélanie, Ménand Mickaël, Le Gac Stéphane, Luhmer Michel, Dalla Vincent, Jabin Ivan, Calix[6]tris(thio)ureas: Heteroditopic Receptors for the Cooperative Binding of Organic Ion Pairs, 10.1021/jo800712q
  37. Moerkerke Steven, Ménand Mickaël, Jabin Ivan, Calix[6]arene-Based Cascade Complexes of Organic Ion Triplets Stable in a Protic Solvent, 10.1002/chem.201001193
  38. Moerkerke Steven, Le Gac Stéphane, Topić Filip, Rissanen Kari, Jabin Ivan, Selective Extraction and Efficient Binding in a Protic Solvent of Contact Ion Triplets by Using a Thiourea-Based Bis-Calix[6]arene Receptor : Selective Extraction with a Bis-Calix[6]arene Receptor, 10.1002/ejoc.201300639
  39. Cornut Damien, Moerkerke Steven, Wouters Johan, Bruylants Gilles, Jabin Ivan, A Biomimetic Heteroditopic Receptor for Zwitterions in Protic Media, 10.1002/asia.201403082
  40. Moerkerke Steven, Wouters Johan, Jabin Ivan, Selective Recognition of Phosphatidylcholine Lipids by a Biomimetic Calix[6]tube Receptor, 10.1021/acs.joc.5b01531
  41. Le Gac Stéphane, Zeng Xianshun, Reinaud Olivia, Jabin Ivan, Synthesis and Conformational Study of the First Triply Bridged Calix[6]azatubes, 10.1021/jo048137l
  42. Punzi John S., Banerjee Srabani, Abood Leo G., Structure-activity relationships for various N-alkylcarbamyl esters of choline with selective nicotinic cholinergic properties, 10.1016/0006-2952(91)90548-j
  43. Vasudevamurthy Madhusudan K., Lever Michael, George Peter M., Morison Ken R., Betaine structure and the presence of hydroxyl groups alters the effects on DNA melting temperatures, 10.1002/bip.21085