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水解酶在二乙基锌与芳香醛加成反应中的应用(英文)

Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Hydrolase

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【作者】 魏晓飞郑清川吉腾飞赵博李春元王萍曹淑桂王智王磊

【Author】 WEI Xiaofei1,ZHENG Qingchuan2,JI Tengfei3,ZHAO Bo1,LI Chunyuan1,WANG Ping1,CAO Shugui1,WANG Zhi1,WANG Lei1,1Key Laboratory of Molecular Enzymology and Engineering of Ministry of Education,Jilin University,Changchun 130023,Jilin,China 2State Key Laboratory of Theoretical and Computational Chemistry,Jilin University,Changchun 130023,Jilin,China 3Institute of Materia Medica,Chinese Academy of Medical Sciences,Beijing 100050,China

【机构】 吉林大学分子酶学工程教育部重点实验室吉林大学理论化学计算国家重点实验室中国医学科学院药物研究所

【摘要】 报道了水解酶催化二乙基锌与芳香醛的加成反应,对反应条件进行了优化.在最适条件(嗜热酯酶APE1547为酶源,反应温度40oC,氯仿为溶剂,4-Cl-苯甲醛为底物)下,加成反应生成的光学活性醇产率最高达78%,ee值最高可达56%.通过实验结果和分子动力学分析对可能的反应机理进行了推测.本研究进一步拓展了酶的非专一性.

【Abstract】 A novel application of hydrolase as catalyst for the addition of diethylzinc to aromatic aldehydes is reported.Optimum conditions were screened out.Under the optimum conditions(i.e.,reaction at 40 oC using hyperthermophilice esterase APE1547,4-Cl-benzaldehyde substrate,and trichloromethane solvent),this reaction provided optically active secondary alcohol with an enantiomeric excess up to 56% and a yield up to 78%.The possible mechanism was proposed based on experimental observations and molecular dynamics simulation.These observations extend the phenomenon of enzyme promiscuity.

【关键词】 水解酶二乙基锌芳香醛加成非专一性
【Key words】 hydrolasediethylzincaromatic aldehydeadditionenzymepromiscuity
【基金】 Supported by the National Natural Science Foundation of China (20803028);Science Technology Development Program of Jilin Province for Youths (20080149)
  • 【文献出处】 催化学报 ,Chinese Journal of Catalysis , 编辑部邮箱 ,2009年05期
  • 【分类号】O643.32
  • 【被引频次】2
  • 【下载频次】84
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