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2013 Chemistry Newsletter
The Department of Chemistry Newsletter is now available.
Read 2013 Newsletter
2013 Beckman Scholars Program
The UO Chemistry Department will be awarding prestigious Beckman Research Scholarships to qualifying undergraduate research students. 2013 Beckman Scholars Information
B.S., University of Oregon, 2004. Ph.D., University of California, Berkeley, 2008 (Robert G. Bergman and Kenneth N. Raymond). Postdoctoral: Massachusetts Institute of Technology, 2008-11 (Stephen J. Lippard). Honors and Awards: Barry M. Goldwater Scholar, 2003-04; NSF Graduate Research Fellow, 2004-07; ACS Young Investigator Award, 2008; NIH National Research Service Award, 2008-10; NIH Pathway to Independence Award, 2010.
Molecular recognition, defined by functional group complementarily, confinement, encapsulation, and self-assembly, is a powerful driving force behind many chemical events. These selective, yet sometimes unpredictable, interactions have been translated into different chemistries ranging from sensing to catalysis. Research in the Pluth group focuses on extending traditional uses of molecular recognition by the rational design of systems poised to activate small molecules. Specifically, our research focuses on the development of fluorescent probes for biological analytes and the self-assembly and allosteric regulation of transition metal catalysts for performing selective organic transformation.
Small molecule fluorescent probes for endogenous gasotransmitters: One main focus of the group is to develop biocompatible luminescent sensors for gasotransmitters produced endogenously. The study of signal transducing gasotransmitters has evolved over the past twenty years based on the discovery that gaseous molecules are biosynthesized and involved in numerous signaling and potentiation processes. After the discovery in 1987 that biosynthetic nitric oxide was the endothelium-derived relaxing factor, two other endogenous gases, namely carbon monoxide and, most recently, hydrogen sulfide (H2S), have garnered interest as biosynthetic gaseous signaling molecules. Despite this interest, current methods of H2S detection lack spatial or temporal resolution and only provide mean bulk measurements of this important molecule, consequently hindering the advancement of detailed studies of its biological function. By using the unique chemical properties of H2S, novel strategies are being used to develop bright, selective fluorescent probes for hydrogen sulfide. Such probes will provide new tools to study and understand the emerging roles of hydrogen sulfide in biology.
Self-assembled ligands for catalysis and catalytic regulation: A second research program in the group focuses on developing catalysts that self-assemble from simple organic and inorganic components and to study the regulation of such catalytic systems. Nature has evolved to seamlessly combine molecular recognition and catalysis to carry out remarkable transformations. Over the past few decades, the fields of transition metal catalysis and supramolecular chemistry have provided synthetic chemists with a diverse palette of new selective transformations and a toolbox for the construction of molecules through complementary interactions, respectively. Despite the concomitant and rapid growth of both of these disciplines, the interface between these fields remains underexplored. As the demand for more efficient catalysts has increased, the need for new, often asymmetric, structurally diverse ligands has also increased. Despite these needs, as chemists we still lack the ability to accurately and reproducibly predict chemical selectivity a priori based on ligand structure. To achieve chemical selectivity and to screen for new reactivity, chemists often rely on libraries of synthetically laborious ligands. By using principles from supramolecular chemistry and molecular recognition, the Pluth group utilizes diverse self-assembling multi-component ligands for use in transition metal catalysis. This method not only provides access to a large multiplicative ligand library, but also offers a unique platform by which ligand components can participate in allosteric regulation. In addition to developing new synthetic methods, we are also interested in understanding the key mechanistic steps required for such self-assembly processes in its relation to allosteric catalytic regulation and autocatalysis.
Students and researchers can look forward to working in an interdisciplinary group with research interests at the interfaces between organic/inorganic chemistry and chemical biology. Research in the group relies on many preparative and analytical techniques ranging from organic and organometallic synthesis to tissue culture preparation and computational chemistry. Physical methods include UV-vis and fluorescence spectroscopy, fluorescence microscopy, X-ray crystallography, advanced multidimensional NMR techniques, and other forms of spectroscopy.
10. Montoya, L.A.; Pearce, T.F.; Hansen, R.J.; Zakharov, L.N.; Pluth, M.D. Development of Selective Colorimetric Probes for Hydrogen Sulfide Based on Nucleophilic Aromatic Substitution. J. Org. Chem. 2013, 78(13), 6550-6557.
9. Montoya, L.A.; Pluth, M.D. Selective Turn-On Fluorescent Probes for Imaging Hydrogen Sulfide in Living Cells. Chem. Commun. 2012, 48(39), 4767-4769
8. Pluth, M.D.; McQuade, L.E.; Lippard, S.J. Cell-Trappable Fluorescent Probes for Nitric Oxide Visualization in Living Cells. Org. Lett. 2010, 12, 2318-2321.
7. Pluth, M.D.; Fiedler, D.; Mugridge, J.S.; Bergman, R.G.; Raymond, K.N. Encapsulation and Characterization of Proton-Bound Amine Homodimers in a Water Soluble, Self-Assembled Supramolecular Host. Proc. Nat. Acad. Sci. USA. 2009, 106, 10438-10443.
6. Pluth, M.D.; Bergman, R.G.; Raymond, K.N. The Acid Hydrolysis Mechanism of Acetals Catalyzed by a Supramolecular Assembly in Basic Solution. J. Org. Chem. 2009, 74, 58-63. (Selected by journal as Featured Article.)
5. Pluth, M.D.; Bergman, R.G.; Raymond, K.N. Supramolecular Catalysis of Orthoformate Hydrolysis in Basic Solution: An Enzyme-Like Mechanism. J. Am. Chem. Soc. 2008, 130, 11423-11429.
4. Pluth, M.D.; Bergman, R.G.; Raymond, K.N. Encapsulation of Protonated Diamines in a Water-Soluble Chiral Supramolecular Assembly Allows for Measurement of Hydrogen-Bond Breaking Followed by Nitrogen Inversion/Rotation (NIR). J. Am. Chem. Soc. 2008, 30, 6362-6366.
3. Pluth, M.D.; Bergman, R.G.; Raymond, K.N. Catalytic Deprotection of Acetals in Basic Solution Using a Self-Assembled Supramolecular 'Nanozyme'. Angew. Chem. Int. Ed. 2007, 119, 8741-8743. (Selected by journal as Very Important Paper).
2. Pluth, M.D.; Robert Bergman, R.G.; Raymond, K.N. Making Amines Strong Bases: Thermodynamic Stabilization of Protonated Guests in a Highly-Charged Supramolecular Host. J. Am. Chem. Soc. 2007, 129, 11459-11467.
1. Pluth, M.D.; Bergman, R.G.; Raymond, K.N. Acid Catalysis in Basic Solution: A Supramolecular Host Promotes Orthoformate Hydrolysis. Science 2007, 316, 85-88. (Subject of Chemical & Engineering News concentrate: 2007, 85, 36.)
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