An Effective Method for Controlling the Stereoselectivity in Asymmetric Reduction of β-Oxo Ester with Yeast Cells
摘要:
Using the reduction of ethyl 4-chloro-3-oxobutanoate (COBE) to enantiomeric pure ethyl 4-chloro-3-hydroxybutanoate (CHBE) as the model reaction, the method for controlling the stereoselectivity of reduction of β-oxo esters by pretreatment of the yeast was studied. The primary technique was pretreatment of the yeast cells with enzyme inhibitors, such as allyl alcohol and allyl bromide, for a period before asymmetric transformation of COBE. It was found that the stereoselectivity of the reduction reaction could be controlled to produce S-CHBE when the yeast cells were pretreated with allyl alcohol. The ee of S-CHBE was improved with increasing the concentration of allyl alcohol and the pretreatment time. 95% for ee of S-CHBE could be reached when allyl alcohol was 1 g/L and pretreatment time was 2 h. On the contrary, the pretreatment with allyl bromide could turn the stereoselectivity of this reduction reaction from S-CHBE to R-CHBE. Also the inhibitor concentration and pretreatment time had positive effect on ee of R-CHBE. And the ee of R-CHBE could reach to 98% when an appropriate condition was applied.
展开
关键词:
asymmetric reduction chiral alcohol yeast cell biocatalysis ethyl 4-chloro-3-oxobutanoate ethyl 4-chloro-3-hydroxybutanoate
被引量:
年份:
2004
通过文献互助平台发起求助,成功后即可免费获取论文全文。
相似文献
参考文献
引证文献
来源期刊
引用走势
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用!