Department of Chemistry
Faculty, Graduate Program
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.
Ph.D., Organic Chemistry, Massachusetts Institute of Technology, 1970
Evans Award, Ohio State University, 2006
Univ. of Oregon Creativity Award in Chemistry, Dance and Music, 2007
Tau-Shue Chou Award, Academica Sinica, 2008
A. von Humboldt Senior Scientist Award, Germany, 2009
Fellow, Royal Society of Chemistry, 2009
Israeli Chemical Society, Honorary Member, 2009
Honorary Doctorate, University of Bonn, 2010
Nichols Medal, ACS New York Section, 2011
Recent Named Lectureships:
Wyeth Lecturer, Princeton University, 2006
Marker Lecturer, University of Maryland, 2007
Haberman Lecturer, Marquette University, 2007
Joullie Lecturer, University of Pennsylvania, 2008
Tau-shue Chou Lecturer, Taipei, Taiwan, 2008
Frontiers in Chemistry, Case Western Reserve, 2009
Allergan Distinguished Lecturer, California State University, Long Beach, 2009
Frontiers of Chemistry Lectures, Texas A&M University, 2010
Kohler Lectures, UC Riverside 2010
Current Editorial Advisory Boards, Tetrahedron Publications:
Bioorganic and Medicinal Chemistry Letters; Bioorganic and Medicinal Chemistry; Journal of the Chemical Society Perkin Transactions; Chemistry and Biology; Journal of Organic Chemistry; Current Opinion in Chemistry Biology; Progress in Physical Organic Chemistry; Journal of Supramolecular Chemistry.
S.R. Shenoy, F.R. Pinacho Crisostomo, T. Iwasawa, J. Rebek, Jr. Organocatalysis in a synthetic receptor with an Inwardly-Directed Carboxylic Acid. J. Am. Chem. Soc. 2008, 130, 5658-5659. PMID: 18393498
D. Ajami, J. Rebek, Jr. Compressed Alkanes in Reversible Encapsulation Complexes. Nature, Chem, 2009, 1, 87-90. PMID: 21378806
T. J. Dale, J. Rebek, Jr. Hydroxy Oximes as Organophosphorus Nerve Agent Sensors. Angew. Chem. Int. Ed., 2009, 48, 7850-7852. PMID: 19757467
A. Sather, O. Berryman and J. Rebek, Jr. Selective Recognition and Extraction of the Uranyl Ion J. Am. Chem. Soc. 2010, 132, 13572-13574. PMID: 20839791
A. Lledo, S. Kamioka, A. Sather and J. Rebek, Jr. Supramolecular Architecture with a Cavitand – Capsule Chimera. Angew. Chem. Int. Ed., 2011, 50, 1299-1301. DOI: 10.1002/anie.201006166. PMID: 21290497