Environmentally Benign Synthesis of Aromatics from Carbohydrates

密歇根州立大学化学系的John Frost教授因其对从碳水化合物合成芳烃的环境友好的研究而得到有机合成项目的支持。 对于对微生物有毒的芳族靶标，Frost教授开发了混合合成，其中碳水化合物向无毒的氢化芳族中间体的微生物转化之后是化学（即，非生物）转化为所需的芳族产物。 因此，例如，E.大肠杆菌被改造为生产奎尼酸，然后在体外转化为氢醌。 遵循相关策略，Frost教授正在探索葡萄糖向没食子酸和肌肌醇的微生物转化，以及将这些中间体分别转化为间苯二酚和1，2，3，4-四羟基苯所需的化学步骤。煤焦油）或通过传统的合成方法，已经认识到对这些重要化合物的新的合成方法的需求。 在有机合成计划的支持下，密歇根州立大学化学系的John Frost教授正在改造微生物，以实现安全和大量可用的原料（例如，葡萄糖）转化为所需的芳香族产物。 在许多情况下，所需产物对实现转化所需的生物体是有毒的。 在这些情况下，弗罗斯特教授开发了“混合”合成，其中微生物被工程化以产生无毒的中间化合物，然后可以在实验室中转化为最终产品。

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.