Enantioselective Synthesis of Silicon Containing Cyanohydrin: (R)-2-trimethylsilyl-2-hydroxyl-ethycyanide by Oxynitrilase from Plum

刘森林; 宗敏华; 黄舜荣

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Enantioselective Synthesis of Silicon Containing Cyanohydrin: (R)-2-trimethylsilyl-2-hydroxyl-ethycyanide by Oxynitrilase from Plum

首发时间：2006-05-18

Liu Senlin ¹ Zong Minhua ¹ Huang Shunrong ¹

1、College of Life Science, Shenzhen University

Abstract：The enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin catalyzed by (R)-oxynitrilases from plum seed meal in an aqueous/organic biphasic system for the preparation of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide was successfully carried out. For optimization of the reaction, the influences of some important factors on the plum oxynitrilase-catalyzed reaction were investigated. Diisopropyl ether was found to be the best organic phase for the reaction among all the organic solvents explored. The optimal buffer pH and aqueous phase content were 5.0 and 13% (V/V), respectively, under which substrate conversion and product enantiomeric excess were 99% and 99%, respectively.

keywords： Enantioselective synthesis Ketone-cyanohydrin (R)-Oxynitrilase (R)-2-Trimethylsilyl-2-hydroxyl-ethylcyanide Organosilicon

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Enantioselective Synthesis of Silicon Containing Cyanohydrin: (R)-2-trimethylsilyl-2-hydroxyl-ethycyanide by Oxynitrilase from Plum

刘森林 ¹ 宗敏华 ¹ 黄舜荣 ¹

1、深圳大学生命科学学院

摘要：The enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin catalyzed by (R)-oxynitrilases from plum seed meal in an aqueous/organic biphasic system for the preparation of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide was successfully carried out. For optimization of the reaction, the influences of some important factors on the plum oxynitrilase-catalyzed reaction were investigated. Diisopropyl ether was found to be the best organic phase for the reaction among all the organic solvents explored. The optimal buffer pH and aqueous phase content were 5.0 and 13% (V/V), respectively, under which substrate conversion and product enantiomeric excess were 99% and 99%, respectively.

关键词： Enantioselective synthesis; Ketone-cyanohydrin; (R)-Oxynitrilase; (R)-2-Trimethylsilyl-2-hydroxyl-ethylcyanide; Organosilicon

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1. 高等学校博士学科点专项科研基金资助课题（20030561017）

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Liu Senlin,Zong Minhua,Huang Shunrong. Enantioselective Synthesis of Silicon Containing Cyanohydrin: (R)-2-trimethylsilyl-2-hydroxyl-ethycyanide by Oxynitrilase from Plum[EB/OL]. Beijing:Sciencepaper Online[2006-05-18]. http://www.paper.edu.cn/releasepaper/content/200605-205.

No.6678649901147923****

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论文编号	200605-205
论文题目	Enantioselective Synthesis of Silicon Containing Cyanohydrin: (R)-2-trimethylsilyl-2-hydroxyl-ethycyanide by Oxynitrilase from Plum
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