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Asymmetric Synthesis of (R)-2-trimethylsilyl-2-hydroxyl- propionitrile by (R)-oxynitrilase from Prunus Japonica
Wu Hong #,Zong Minhua *,Huang Shunrong
South China University of Technology
*Correspondence author
#Submitted by
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Funding: 教育部博士点基金(No.20030561017)
Opened online:23 October 2006
Accepted by: none
Citation: Wu Hong,Zong Minhua,Huang Shunrong.Asymmetric Synthesis of (R)-2-trimethylsilyl-2-hydroxyl- propionitrile by (R)-oxynitrilase from Prunus Japonica [OL]. [23 October 2006] http://en.paper.edu.cn/en_releasepaper/content/8912
 
 
Optically active silicon containing cyanohydrin: (R)-2-trimethylsilyl-2-hydroxyl- propionitrile was successfully synthesized by asymmetric transcyanation of acetyltrimethylsilane with acetone cyanohydrin in an aqueous/organic biphasic system catalyzed with (R)-oxynitrilase from defatted Prunus Japonica seed meal. Various influential variables were examined for better understanding of the reaction. Diisopropyl ether was found to be the best organic phase for the reaction among all the organic solvents explored. The optimum concentrations of acetyltrimethylsilane and acetone cyanohydrin, volume ratio of aqueous phase to organic phase, buffer pH value and the reaction temperature were 14 mmol ∙ L–1, 28 mmol ∙ L–1, 13% (by volume), 5.0 and 30 oC, respectively. Under the above optimal conditions, the initial reaction rate, the substrate conversion and the product enantiomeric excess were 1.34 mmol∙L–1 ∙ h–1, 99.0% and 99.0%, respectively.
Keywords:(R)-oxynitrilase; asymmetric transcyanation; acetyltrimethylsilane; (R)-2-trimethylsilyl-2-hydroxyl-propionitrile
 
 
 

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