Explorations in Organosulfur Chemistry

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Every inventor requires a background database of knowledge from which they draw information. That information is combined with the inventor's idea, imagination and skill to produce a new process or product. If the database of information was not able to grow, inventors would soon run out of new intellectual "raw materials" that are so essential to the inventive puzzle. In time, our society would no longer be economically, technologically or culturally progressive. In the chemical field, inventions often include new pharmaceuticals, materials, food products and new products for the home and farm. Inventions could also include new processes to produce established products by substantially more economical and/or environmentally friendly methods. The chemistry database contains, for example, information regarding fundamental chemical reactions and theories of bonding in chemistry. In the Schwan group we unveil fundamental reactivity of sulfur containing organic compounds. The following fundamental studies will expand the organic chemistry database in general, but also have application to the food and spice industries and to the pharmaceutical industry. 1. The proposed chemistry will expand our knowledge of how existing one particular family of sulfur compounds called sulfenates can be influenced as they are reacted to make carbon-sulfur bonds. The influences arise from the presence of other atoms within the same molecule, or in a co-reactant. We will probe the role of oxygen, nitrogen and boron atoms to learn how they direct the sulfenates to make new bonds, and at what rates. 2. Some of the unique flavors of the shiitake mushrooms arise from the metabolites containing sulfur atoms. We are proposing the preparation of the precursor of the flavorants and in doing so, will demonstrate a new sequence of reactions. The preparation should facilitate an increased understanding of its chemical conversions to the flavor compounds of the mushroom and the enzymes involved in those processes. 3. The pursuit of new pharmaceutical substances often requires one to synthesize previously unknown chemical structures. We plan to delve into this area by pursuing the preparation of new small molecules containing sulfur and nitrogen atoms in a novel relative arrangement. These molecules will then be explored for their reactivity, with the intention of creating larger, more drug-like molecules. A successful outcome will be a selection of new molecules with potential to show desirable biological properties.