Catalysis and molecular recognition

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Understanding the nature of the bonds that hold atoms together in molecules has been a primary goal of chemists since the earliest days of the field. However, a second type of interaction is equally important to understanding chemical behavior: these are 'intermolecular interactions', the forces that act between molecules. All phenomena that involve pairs or groups of molecules in contact - for example, the behavior of liquid water, or the binding of a drug molecule to its target - are influenced by these forces. Our research is aimed at understanding and exploiting intermolecular interactions. We use interactions between boron compounds and sugars as the basis for new types of chemical reactions. Boron compounds bind with predictable selectivity to particular sites in sugars. Supported by this Discovery Grant, we aim to use this type of binding to trigger chemical reactions of sugars at specific positions. Such reactions will provide ways to rapidly and efficiently prepare the complex, carbohydrate-containing molecules that play key roles in cell-cell and cell-pathogen interactions, thus facilitating the development of carbohydrate-based biochemical tools and therapeutic agents. In addition, we will develop boron-based processes for the preparation of polymers (plastics) from sugar derivatives. Not only are carbohydrate-derived polymers based on abundant, renewable feedstocks, but they are also biodegradable and non-toxic, key advantages for biomedical and drug delivery applications. The other goal of our research program is to gain fundamental insight into poorly understood intermolecular interactions of the halogens (chlorine, bromine and iodine) and chalcogens (sulfur and related elements). We will design and synthesize molecules that allow us to determine the strengths of these interactions. This type of information is crucial for understanding how they can be applied in drug design, materials science and chemical reactivity. The students who carry out this research will build expertise in organic synthesis (how to design, execute and optimize chemical reactions to prepare carbon-based compounds), while broadening their training through exposure to the techniques and concepts of polymer chemistry, along with analytical and computational methods. This skill set will position them strongly for employment in a wide range of sectors, including in the pharmaceutical, biotech, agrochemical and polymer chemistry industries.