Using water-miscible ionic liquids to improve the biocatalytic anti-Prelog asymmetric reduction of prochiral ketones with whole cells of Acetobacter sp. CCTCC M209061
Using water-miscible ionic liquids to improve the biocatalytic anti-Prelog asymmetric reduction of prochiral ketones with whole cells of Acetobacter sp. CCTCC M209061
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使用与水混溶的离子液体改善醋杆菌全细胞对前手性酮的生物催化抗Prelog不对称还原。
DOI：
10.1016/j.ces.2012.09.019
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发表时间：
2012-12
影响因子：
4.7
通讯作者：
Zong, Min-Hua
中科院分区：
文献类型：
--
作者：
Xiao, Zi-Jun;Du, Peng-Xuan;Lou, Wen-Yong;Wu, Hong;Zong, Min-Hua
通过用醋杆菌全细胞对酮进行反Prelog不对称还原，成功地利用亲水性离子液体来改进对映体纯醇的合成。 CCTCC M209061 新从中国开菲尔中分离出来。 C2OHMIM·NO3的效果最好，显示出良好的生物相容性，并且还适度增加了细胞膜的通透性，从而提高了反应效率。此外，4-(三甲基硅基)-3-丁炔-2-一还原成(R)-4-(三甲基硅基)-3-丁炔-2-醇的最佳C2OHMIM·NO3含量、缓冲液pH、反应温度和底物浓度分别为10.0% (v/v)、5.0、30°C和12 mM。在优化条件下，初始反应速率、最大产率和产物e.e.分别为14.0μmol/min·gcell、91%和>99%，比之前报道的结果要好得多。高效的全细胞生物催化工艺在400 mL制备规模上被证明是可行的，并且固定化细胞在连续重复使用10批后仍保留88.0%以上的原始活性，在C2OHMIM·NO3存在下表现出良好的操作稳定性。此外，还建立了醋杆菌生物催化系统。 CCTCC M209061 和 C2OHMIM·NO3 对于其他芳基酮向相应 (R)-醇的反 Prelog 不对称还原非常有效。
The utilization of hydrophilic ionic liquids to improve the synthesis of enantiopure alcohols was successfully performed, via the anti-Prelog asymmetric reduction of ketones with whole cells of Acetobacter sp. CCTCC M209061 newly isolated from Chinese kefir. The best results were obtained with C2OHMIM·NO3, which showed good biocompatibility and also increased moderately cell membrane permeability, thus improving the reaction efficiency. Additionally, the optimal C2OHMIM·NO3content, buffer pH, reaction temperature and substrate concentration for 4-(trimethylsilyl)-3-butyn-2-one reduction to (R)-4-(trimethylsilyl)-3-butyn-2-ol were 10.0% (v/v), 5.0, 30°C and 12mM, respectively. Under the optimized conditions, the initial reaction rate, the maximum yield and the product e.e. were 14.0μmol/min·gcell, 91%, and >99%, respectively, which were much better than the results reported previously. The efficient whole-cell biocatalytic process proved to be feasible on a 400-mL preparative scale, and the immobilized cells still retained above 88.0% of their original activity after successive re-use for 10 batches, showing the good operational stability in the presence of C2OHMIM·NO3. Furthermore, the established biocatalytic system with Acetobacter sp. CCTCC M209061 and C2OHMIM·NO3was shown to be highly effective for the anti-Prelog asymmetric reduction of other aryl ketones to the corresponding (R)-alcohols.
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影响因子：
3.2
作者：
G. Charlang;N. Horowitz
通讯作者：
G. Charlang;N. Horowitz
影响因子：
2.2
作者：
Hoefel, D;Grooby, WL;Saint, CP
通讯作者：
Saint, CP
影响因子：
3.4
作者：
Li, Yong-Ning;Shi, Xian-Ai;Guo, Yang-Hao
通讯作者：
Guo, Yang-Hao
影响因子：
15
作者：
Kaar, JL;Jesionowski, AM;Russell, AJ
通讯作者：
Russell, AJ
影响因子：
4.1
作者：
Lou, Wen-Yong;Zong, Min-Hua;Wang, Ju-Fang
通讯作者：
Wang, Ju-Fang