Enviromentally Benign Synthesis of Aromatic Chemicals from Carbohydrates

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The focus of this work is fourfold. First, methodology will be developed whereby biocatalytically synthesized inositol hydroaromatics are abiotically converted into pyrogallol, phloroglucinol, hydroxyhydroquinone, hydroquinone, catechol and resorcinol. Second, the uptake of D-glucose in E. coli will be altered to increase the percent yield of D-glucose into 3-dehydroshikimic acid, a key intermediate in the biocatalytic synthesis of adipic acid, catechol and gallic acid. Third, a biocatalytic route to hydroquinone will be created by expressing the P. chrysosporium gene encoding vanillate hydroxylase in p-hydroxybenzoate-synthesizing E. coli. Fourth, a biocatalytic synthesis of resorsinol will be developed using genes encoding gallate-synthesizing and gallate-degrading enzymes from P. blakesleeanus, K. pneumoniae, P. acidigallici and E. oxidoreducens. With this Environmentally Benign Chemical Synthesis and Processing award, the Synthetic Organic Program is supporting the research of Dr. John W. Frost of the Department of Chemistry at Michigan State University. Dr. Frost will focus his work on developing synthetic methodology that allows a variety of chemicals to be economically derived from carbohydrate feedstocks. In this way, nontoxic D-glucose, D-xylose and L-arabinose, derived from renewable corn starch and fiber, can replace carcinogenic benzene, derived from nonrenewable fossil fuels, as a synthetic starting material.