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Highly enantioselective resolution of racemic 1-phenyl-1,2-ethanediol to (S)-1-phenyl-1,2-ethanediol by Kurthia gibsonii SC0312 in a biphasic system.
Journal of Biotechnology ( IF 4.1 ) Pub Date : 2019-11-20 , DOI: 10.1016/j.jbiotec.2019.11.012
Fei Peng 1 , Ying Zhao 1 , Fang-Zhou Li 1 , Xiao-Yang Ou 1 , Ying-Jie Zeng 1 , Min-Hua Zong 1 , Wen-Yong Lou 1
Affiliation  

The asymmetric resolution of racemic 1-phenyl-1,2-ethanediol (PED) to (S)-PED by Kurthia gibsonii SC0312 (K. gibsonii SC0312) was conducted in a biphasic system comprised of an organic solvent and aqueous phosphate buffer. The impacts of organic solvents on the whole cell catalytic activity, metabolic activity, membrane integrity, and material distribution were first evaluated. The results showed that all organic solvents, except for dibutyl phthalate, showed a detrimental effect on the metabolic activity of the cells, especially for those with low log P values. All organic solvents were capable of changing the membrane permeability and membrane integrity of the cells. Moreover, some organic solvents showed a good extraction of the oxidation product. Finally, a high yield of 47.7 % of (S)-PED was obtained by the asymmetric resolution of racemic PED using K. gibsonii SC0312 in a biphasic system under the optimal conditions: racemic PED 120 mM, temperature 35 °C, reaction time 6 h, 180 rpm, and a volume ratio of dibutyl phthalate to aqueous phosphate buffer of 1:1. The optical purity of (S)-PED increased from 51.3 % to >99 %. This work described an efficient approach to improve reaction efficiency, and constructed a highly effective biphasic reaction system for the fabrication of (S)-PED via K. gibsonii SC0312.

中文翻译:

在两相系统中,Kurthia gibsonii SC0312对外消旋的1-苯基-1,2-乙二醇对(S)-1-苯基-1,2-乙二醇的高度对映选择性拆分。

Kurthia gibsonii SC0312(K. gibsonii SC0312)的外消旋1-苯基-1,2-乙二醇(PED)与(S)-PED的不对称拆分是在由有机溶剂和磷酸盐水溶液构成的双相体系中进行的。首先评估了有机溶剂对全细胞催化活性,代谢活性,膜完整性和材料分布的影响。结果表明,除邻苯二甲酸二丁酯外,所有有机溶剂均对细胞的代谢活性产生有害影响,特别是对于那些log P值较低的细胞。所有有机溶剂均能够改变细胞的膜通透性和膜完整性。而且,一些有机溶剂显示出良好的氧化产物萃取。最后,高产47。在以下最佳条件下,使用吉布森氏菌SC0312在双相系统中,通过外消旋PED的不对称拆分,可得到7%(S)-PED:外消旋PED 120 mM,温度35°C,反应时间6 h,180 rpm和邻苯二甲酸二丁酯与磷酸盐水溶液的体积比为1:1。(S)-PED的光学纯度从51.3%增加到> 99%。这项工作描述了一种提高反应效率的有效方法,并构建了一种高效的双相反应体系,用于通过吉氏梭菌SC0312制备(S)-PED。
更新日期:2019-11-01
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