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研究领域

Research Focus Molecular Studies Studies in molecular recognition and catalysis We have developed a series of synthetic receptors for small biorelevant molecular targets. These systems are container molecules, deep cavitands, that more-or-less surround the targets and present them with functional groups. This arrangement allows isolation and direct observation of reactive intermediates and catalysis of reactions with large rate enhancements. Molecular self-assembly and encapsulation We introduced a series of molecular capsules which self-assemble in the presence of appropriate guest species. These have been prepared in a variety of shapes and sizes, from those appropriate for encapsulation of methane to those capable of encapsulating transition states of cycloaddition reactions. The capsules reveal the behavior of molecules in very small spaces and channel their reactions along previously unknown pathways. The capsules and cavitands represent the leading edge of techniques in physical organic chemistry and provide new sequestering agents for actinide ions. Sensors and antidotes for chemical warfare agents We have devised a means by which a large number of nerve agents are rapidly detected and detoxified. The tactic involves combining a fluorescent dye with a reactive nucleophile such as an oxime. Reaction with a nerve agent is followed by a rapid intramolecular cyclization that creates a new fluorophore and destroys the agent. Current research revolves around the selective recognition of agents and their destruction in a catalytic manner. Protein surface mimetics We have synthesized small molecule scaffolds that present amino acid side chains that mimic arrangements found in protein alpha helices and beta strands. We have prepared some structures that act as agonists for neuropeptide receptors and others that target proteins involved in innate immunity. Current research involves the design of structures that will interfere with the inflammation cascade that leads to sepsis.

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J. Kubitschke, S. Javor and J. Rebek, jr., "Deep Cavitand Vesicles-Multicompartmental Hosts" Submitted T. Taira, D. Ajami and J. Rebek, Jr., "Hydration of Isocyanates in an Expandable, Self-assembled capsule" Chem Commun, 2012, in press A. Asadi, D. Ajami and J. Rebek, "Reversible Encapsulation with Covalent Structures" Submitted S. Javor, A. Janowsky, R. Johnson, K. Wolfrum, M. Tadayoni-Rebek, and J. Rebek, Jr. , "Formylated Polyamine Peptidomimetic" Submitted W. Jiang, K. Tiefenbacher, D. Ajami and J. Rebek, Jr, "Complexes within complexes: Hydrogen bonding in capsules" submitted T. Taira, D. Ajami and J. Rebek, Jr. , "Encapsulation of ion pairs in extended, self-assembled structures" J. Am. Chem. Soc., 2012, in press D. Ajami and J. Rebek, Jr. , "More chemistry in small spaces" Acc. Chem Res., 2012, in press T. L. Kissner; G. Ruthel; S. Alam; E. Mann; D. Ajami; M. Rebek; E. Larkin; S. Fernandez; R. G. Ulrich; S. Ping; D. S. Waugh; J. Rebek, Jr.; K. U Saikh, , "Therapeutic Inhibition of Pro-inflammatory Signaling and Toxicity to Staphylococcal Enterotoxin B by a Synthetic Dimeric BB-loop Mimetic of MyD88" PLos ONE, 2012, in press W. Jiang, D. Ajami and J. Rebek, jr. , "Alkane lengths determine encapsulation rates and equilibria" J. Am. Chem. Soc., 2012, 134, 8070-8073 A. Sather, O. B. Berryman and J. Rebek, Jr., "Synthesis of Fused Indazole Ring Systems and Application to Nigeglanine Hydrobromide" Org. Lett, 2012, 14, 1600-1603 D. Ajami and J. Rebek, jr. , "Reversibly Expanded Encapsulation Complexes" Top Curr Chem, 2012, 319, 57-78 D. Tzeli, G. Theodorakopoulos, I. D. Petsalakis, D. Ajami, J. Rebek, Jr. , "Theoretical study of free and encapsulated carboxylic acid and amide dimers " Int. J. Quantum Chem., 2012, submitted D. Tzeli, G. Theodorakopoulos, I.D. Petsalakis, D. Ajami and J. Rebek, Jr., , "Conformations and fluorescence of encapsulated stilbene" J. Am. Chem. Soc., 2012, 134, 4346-4354 K. Tiefenbacher and J. Rebek, Jr. , "Selective stabilization of self-assembled hydrogen-bonded molecular capsules through pi-pi interactions" J. Am. Chem. Soc., 2012, 134, 2914-2917 H. Dube and J. Rebek, jr., "Selective guest exchange in encapsulation complexes using different light inputs" Angew. Chem. Int. Ed., 2012, 51, 3207-3210 Y. Liu, T. Taira, M. C. Young, D. Ajami, J. Rebek, Jr, "Protein Recognition by a Self-Assembled Deep Cavitand on a Gold Substrate " Langmuir, 2012, 28, 1391-1398 D. Tzeli, G. Theodorakopoulos, I. Petsalakis, D. Ajami, J. Rebek Jr., , "Theoretical study of hydrogen bonding in homodimers and heterodimers of amide, boronic acid and carboxylic acid, free and in encapsulation complexes " J. Am. Chem. Soc., 2011, 133, 16977-16985 O.B. Berryman, A. C. Sather, and J. Rebek, Jr. , "A deep cavitand with a fluorescent wall functinos as an ion sensor" Org. Lett, 2011, 13, 5232-5235 O. B. Berryman, A. C. Sather, A. Lledó and J. Rebek Jr, "Switchable Catalysis with a Light Responsive Cavitand " Angew. Chem. Int. Ed., 2011, 50, 9400-9403 T. L. Kissner, L.Moisan, E. Mann, S. Alam, G. Ruthel, R. G. Ulrich, M. Rebek, J. Rebek Jr., and K. U. Saikh , "A Small Molecule that Mimics the BB-loop in the Toll/IL-1 Receptor Domain of MyD88 Attenuates Staphylococcal Enterotoxin B Induced Pro-inflammatory Cytokine Production and Toxicity in Mice " J. Biol. Chem, 2011, 286, 31385-31396

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