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AMINO ACIDS, POLYMERS, BIOCHEMISTRY AND ORGANIC SYNTHESIS

Synthesis of Addition Polymers

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Transition Metal Chemistry; 9653 - Polymers: Synthesis to Function;

A recent addition to our repertoire is Umpolung Amide Synthesis (UmAS), and its use to prepare α-amino acids, and their polymers – peptides – using fully enantioselective means. This expands our ability to prepare non-natural amino acids considerably, as we have developed methods previously to prepare indoline α-amino acids, constrained proline derivatives, α,β-diamino acids, and α-amino phosphonic acids. Based on these unique skills, we find ourselves drawn further to problems in bioorganic chemistry.

Access information about the Polymer Chemistry Group, University of Queensland

Students in the Gilroy group will work in a highly multidisciplinary environment. The ability to synthesize (and characterize) a wide range of molecular and macromolecular materials, including air- and moisture-sensitive examples, will be complemented by exposure to high-tech materials characterization techniques. Examples of such methodologies include: electrochemistry, magnetochemistry, electron and atomic force microscopy, gel permeation chromatography (GPC), and X-ray crystallography and scattering techniques.

Polymer Chemistry - American Chemical Society

Our programs are tied by the common theme of organic synthesis. We are interested in the development of new reactions and reagents for natural product total synthesis, and we have contributed a variety of new reactions to the chemist's arsenal, including free radical-mediated aryl and vinyl amination, the Brønsted acid-catalyzed aza-Darzens reaction, and a new acid catalyzed olefin aminoacyloxylation reaction. We also apply these reactions to the targets that inspired them. For example, our synthesis of mitomycin C uses the acid-catalyzed aza-Darzens reaction, in addition to a regioselective enamine-quinone coupling. And in our approach to (+)-zwittermicin A, we deploy a variation of our Brønsted acid catalyzed azide-olefin addition. As a result, we are able to synthesize highly functionalized, stereochemically dense advanced intermediates with considerable brevity. We reported the first total synthesis of (+)-serratezomine A using the free radical-mediated vinyl amination reaction, which provided this challenging target in a mere 15 steps (longest linear sequence).

Finally, we have established several new collaborative projects with Vanderbilt investigators in the broad area of medicinal chemistry. These are based on our use of chiral proton catalysis to prepare chiral nonracemic secondary amines, and their conversion to promising therapeutics for Chagas disease, and investigational new drugs like (–)-Nutlin-3 (Hoffmann-La Roche).

American Chemical Society: Chemistry for ..

Research in the Gilroy group focuses on the design and synthesis of inorganic and polymeric materials with interesting conducting, magnetic, redox, and sensing properties. We design our materials, which are prepared as part of an iterative approach, with natural resource sustainability and alternative energy technologies in mind.

Through these studies, the student is trained how to think about problems in organic chemistry from an approach that involves extensive laboratory experimentation. Germane to this training is the routine use of spectroscopic (NMR, IR, mass spectroscopy, X-ray diffraction) and analytical (chiral stationary phase HPLC) techniques. Many of these projects require the student to draw knowledge from an extensive body of literature in organic chemistry while developing truly novel reactions and the reagents (catalysts) that promote them with high levels of stereocontrol. Furthermore, our approach to the development of new chemistry follows a highly synergistic combination of informed design, mechanistic organic chemistry, empiricism, and at times, a touch of luck.

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the type of monomer residues comprising the polymer

We have substantial expertise in synthetic polymer chemistry, including living radical polymerisation chemistries such as ATRP and RAFT. One major theme is the synthesis and aqueous solution characterisation of controlled-structure stimulus-responsive polymers based on hydrophilic methacrylic monomers for a wide range of applications.

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