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Highly Efficient Synthesis of Silicon-Containing (R)-Ketone-Cyanohydrin Catalyzed by (R)-Hydroxynitrilase Lyase from Prunus Domestic
Abstract:
The synthesis of chiral silicon-containing (R)-ketone-cyanohydrin by enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin was efficiently carried out using defatted Prunus domestic seed meal as (R)-hydroxynitrilase lyase for the first time. Under the optimal conditions including a reaction temperature of 25-35°C and a buffer pH of 5.0-5.4, both acetyltrimethylsilane conversion and enantiomeric excess of the product were above 99%. In contrast, this enzyme did not accepted its carbon counterpart 3,3-dimethyl-2-butanone as substrate. These results demonstrated that the silicon atom in substrate served as a more effective atom than the carbon atom to enhance the activity of the enzyme.
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1494-1497
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May 2011
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© 2011 Trans Tech Publications Ltd. All Rights Reserved
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