文献类型：期刊文献

英文题名：Facile Synthesis of Enantiopure 4-Substituted 2-Hydroxy-4-butyrolactones using a Robust Fusarium Lactonase

作者：Chen, Bing[1];Yin, Hai-Feng[2];Wang, Zhen-Sheng[2];Xu, Jian-He[1];Fan, Li-Qiang[1];Zhao, Jian[1]

机构：[1]E China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[2]PepTech Corp Shanghai, Dept Chem, Shanghai 200231, Peoples R China

年份：2009

卷号：351

期号：17

起止页码：2959

外文期刊名：ADVANCED SYNTHESIS & CATALYSIS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000272392000027)，CCR-EXPANDED(收录号:WOS:000272392000027)】；

基金：This research was financially supported by National Natural Science Foundation of China (grant nos. 20506037 and 20773038), Ministry of Science and Technology (grant nos. 2007AA027225 and 2009CB724706), and China National Special Fund for State Key Laboratory of Bioreactor Engineering (grant no. 2060204).

语种：英文

外文关键词：chemo-enzymatic process; circular dichroism; Fusarium proliferatum lactonase; stereoselectivity; 4-substituted 2-hydroxy-4-butyrolactones

摘要：A facile chemo-enzymatic process has been developed for producing stereoisomers of 4-substituted 2-hydroxy-4-butyrolactones with good to excellent enantioselectivity. This process involves an easy separation of the diastereoisomers by column chromatography and efficient enzymatic resolution by whole cells of Escherichia coli JM109 expressing Fusarium proliferatum lactonase gene. This biocatalyst shows strong tolerance towards different substrate structures and at least three out four possible isomers could be obtained in excellent enantiomeric purity. Different substrate concentrations (10 mM-200 mM) were examined, giving a substrate to catalyst ratio of up to 26:1. This general and efficient enzymatic process provides access to stereoisomers of 4-substituted 2-hydroxy-4-butyrolactones readily and cost-effectively. The stereochemical assignments were conducted systematically based on NMR, X-ray diffraction and circular dichroism, leading to further understanding of the enzyme's stereoselectivity.