Environmentally Benign Synthesis of Aromatics from Carbohydrates

本研究的重点是为葡萄糖制备间苯二酚和间苯三酚开辟新的合成路线。利用没食子酸/邻苯三酚、2-脱氧-肌醇/羟基对苯二酚或肌醇-2-肌糖/1，2，3，4-四羟基苯的中间体以及由肌醇和肌糖衍生的六羟基苯和五羟基苯的中间体将被探索。将构建能够高产、高滴度地将葡萄糖转化为没食子酸、肌醇、2-脱氧-肌醇-肌糖和肌醇-2-肌糖的微生物。此外，还将进行实验，比较3-脱氢奎宁、3-脱氢莽草酸和原儿茶酸作为葡萄糖合成儿茶酚的路线在近临界水中的微生物合成和反应。通过这一续展奖项，有机和高分子化学项目支持密歇根州立大学化学系约翰·W·弗罗斯特博士的研究。弗罗斯特教授将把他的工作重点放在设计从碳水化合物前体制备芳香化合物的方法上。这些方法将允许取代有毒的起始物，如苯。这项研究对化学工业和整个环境都有广泛而重要的潜在影响。这项研究也为研究生和博士后提供了一个很好的培训基础。

The focus of this research is to create new synthetic routes for the preparation of resorcinol and phloroglucinol from glucose. A pathway using the intermediacy of gallic acid/pyrogallol, 2-deoxy-scyllo-inosose/hydroxyhydroquinone or myo-2-inosose/1,2,3,4-tetrahydroxybenzene will be explored as will a pathway involving the intermediacy of hexahydroxybenzene and pentahydroxybenzene derived from myo-inositol and myo-2-inosose. Microbes will be constructed that are capable of high-yielding, high-titer conversions of glucose into gallic acid, myo-inositol, 2-deoxy-scyllo-inosose and myo-2-inosose. Also, experiments will be conducted to compare the microbial synthesis and reaction in near-critical water of 3-dehydroquinic, 3-dehydroshikimic and protocatechuic acids as routes for the synthesis of catechol from glucose. With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. John W. Frost of the Department of Chemistry at Michigan State University. Professor Frost will focus his work on devising methodology to prepare aromatic chemicals from carbohydrate precursors. These methods will allow for the replacement of toxic starting materials such as benzene. The research has broad and important potential impact for the chemical industry and for the environment in general. The research also provides an excellent training ground for graduate students and postdoctorals.