Markedly improving asymmetric oxidation of 1-(4-methoxyphenyl) ethanol with Acetobacter sp. CCTCC M209061 cells by adding deep eutectic solvent in a two-phase system. Issue 1 (December 2016)

• Record Type: Journal Article
• Authors: Wei, Ping; Liang, Jing; Cheng, Jing; Zong, Min-Hua; Lou, Wen-Yong
• Is Part Of: Microbial cell factories. Volume 15:Issue 1(2016)
• Page Start: 1
• Page End: 11
• Publication Date: 2016-12
• Subjects: Asymmetric oxidation -- Immobilized Acetobacter sp. CCTCC M209061 cells -- MOPE -- Biphasic system, DES; Microbial biotechnology -- Periodicals; Recombinant proteins -- Synthesis -- Periodicals; 660.62
• DOI: 10.1186/s12934-015-0407-1
• Languages: English
• ISSNs: 1475-2859

Abstract

Abstract Background Enantiopure (S )-1-(4-methoxyphenyl) ethanol {(S )-MOPE} can be employed as an important synthon for the synthesis of cycloalkyl [b ] indoles with the treatment function for general allergic response. To date, the biocatalytic resolution of racemic MOPE through asymmetric oxidation in the biphasic system has remained largely unexplored. Additionally, deep eutectic solvents (DESs), as a new class of promising green solvents, have recently gained increasing attention in biocatalysis for their excellent properties and many successful examples in biocatalytic processes. In this study, the biocatalytic asymmetric oxidation of MOPE to get (S )-MOPE usingAcetobacter sp. CCTCC M209061 cells was investigated in different two-phase systems, and adding DES in a biphasic system was also explored to further improve the reaction efficiency of the biocatalytic oxidation. Results Of all the examined water-immiscible organic solvents and ionic liquids (ILs), 1-butyl-3-methylimidazolium hexafluorophoshpate ([C4 MIM][PF6 ]) afforded the best results, and consequently was selected as the second phase of a two-phase system for the asymmetric oxidation of MOPE with immobilizedAcetobacter sp. CCTCC M209061 cells. For the reaction performed in the [C4 MIM][PF6 ]/buffer biphasic system, under the optimized conditions, the initial reaction rate, the maximum conversion and the residual substratee.e. recorded 97.8 μmol/min, 50.5 and >99.9 % after 10 h reaction. Furthermore, adding the DES [ChCl][Gly] (10 %, v/v) to the aqueous phase, the efficiency of the biocatalytic oxidation was rose markedly. The optimal substrate concentration and the initial reaction rate were significantly increased to 80 mmol/L and 124.0 μmol/min, respectively, and the reaction time was shortened to 7 h with 51.3 % conversion. The immobilized cell still retained over 72 % of its initial activity after 9 batches of successive reuse in the [C4 MIM][PF6 ]/[ChCl][Gly]-containing buffer system. Additionally, the efficient biocatalytic process was feasible up to a 500-mL preparative scale. Conclusion The biocatalytic asymmetric oxidation of MOPE withAcetobacter sp. CCTCC M209061 cells was successfully conducted in the [C4 MIM][PF6 ]-containing biphasic system with high conversion and enantioselectivity, and the reaction efficiency was further enhanced by adding [ChCl][Gly] to the reaction system. The efficient biocatalytic process was promising for the preparation of enantiopure (S )-MOPE.