Environmentally Benign Synthesis of Aromatics from Carbohydrates

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Professor John Frost, of the Department of Chemistry at Michigan State University, is supported by the Organic Synthesis program for his studies of the environmentally benign synthesis of aromatics from carbohydrates. For aromatic targets which are toxic to microbes, Professor Frost develops hybrid syntheses, wherein microbial conversion of carbohydrates to nontoxic hydroaromatic intermediates is followed by chemical (i.e., nonbiological) conversion to the desired aromatic product. Thus, e.g., E. coli is engineered to produce quinic acid, which is then converted in vitro to hydroquinone. Following a related strategy, Professor Frost is exploring the microbial conversion of glucose to gallic acid and myo-inosose, as well as the chemical steps necessary to convert these intermediates to resorcinol and 1,2,3,4-tetrahydroxybenzene, respectively.As the environmental costs of obtaining important commodity aromatic compounds from traditional sources (e.g., coal tar) or via traditional syntheses have been recognized, a need for new synthetic methods for these important compounds has arisen. With the support of the Organic Synthesis Program, Professor John Frost, of the Department of Chemistry at Michigan State University, is engineering microbes to carry out the conversion of safe and abundantly available feedstocks (e.g., glucose) to desired aromatic products. In many cases, the desired product is toxic to the organisms required to effect the conversion. In these cases, Professor Frost develops "hybrid" syntheses, wherein the microbes are engineered to produce a nontoxic intermediate compound which may then be converted in the laboratory to the final product.