Enviromentally Benign Synthesis of Aromatic Chemicals from Carbohydrates

从碳水化合物环境友好地合成芳香族化合物

• 批准号: 9633368
• 负责人: John Frost
• 金额: $ 34.01万
• 依托单位: Michigan State University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1996
• 资助国家: 美国
• 起止时间: 1996-07-01 至 1999-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=9633368&HistoricalAwards=false
• 关键词: Enviromentally; Benign; Synthesis; Aromatic; Chemicals

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.

这项工作的重点有四个。首先，将开发生物催化合成的肌醇氢芳香族化合物非生物转化为邻苯三酚、间苯三酚、羟基氢醌、氢醌、儿茶酚和间苯二酚的方法。 其次，将改变大肠杆菌对 D-葡萄糖的摄取，以提高 D-葡萄糖转化为 3-脱氢莽草酸的百分比产率，3-脱氢莽草酸是己二酸、儿茶酚和没食子酸生物催化合成的关键中间体。 第三，通过在合成对羟基苯甲酸酯的大肠杆菌中表达编码香草酸羟化酶的黄孢青霉基因，将创建对苯二酚的生物催化途径。 第四，将使用来自P. blakesleeanus、K.pneumoniae、P.acidigallici和E.oxyreducens的编码没食子酸盐合成和没食子酸盐降解酶的基因开发间苯二酚的生物催化合成。 凭借这一对环境无害的化学合成和加工奖，合成有机项目正在支持密歇根州立大学化学系的 John W. Frost 博士的研究。 Frost 博士的工作重点是开发合成方法，使各种化学品能够经济地从碳水化合物原料中获得。 这样，源自可再生玉米淀粉和纤维的无毒 D-葡萄糖、D-木糖和 L-阿拉伯糖可以替代源自不可再生化石燃料的致癌苯，作为合成起始材料。