Enzymatic Resolution of Racemic Ethyl-2,2- Dimethylcyclopropanecarboxylate ToS-(+)-2,2- Dimethylcyclopropanecarboxylic Acid in a Polar Organic Solvent—Water Medium

2012 ◽  
Vol 26 (6) ◽  
pp. 3412-3417 ◽  
Author(s):  
Feng Ren ◽  
Pu Wang ◽  
Jin Huang ◽  
Junyao He
Keyword(s):  
Organic Solvent ◽  
Water Medium ◽  
Enzymatic Resolution ◽  
Solvent Water ◽  
Polar Organic Solvent

Micellization in Water-Polar Organic Solvent Binary Mixtures

2011 ◽  
Vol 1 (4) ◽  
pp. 352-368
Author(s):  
Maria Luisa Moya ◽  
Maria del Mar Graciani/snm ◽  
> ◽  
Victoria Isabel Martin
Keyword(s):  
Organic Solvent ◽  
Binary Mixtures ◽  
Polar Organic Solvent

scholarly journals Coordination-Driven Poly[2]Pseudorotaxanes in Highly Polar Organic Solvent

2020 ◽  
Vol 8 ◽  
Author(s):  
Hang Su ◽  
Wei Chen ◽  
Liang Li ◽  
Bin Li ◽  
Zhi-Yuan Zhang ◽  
...  
Keyword(s):  
Organic Solvent ◽  
Polar Organic Solvent

scholarly journals Efficient Biocatalytic Preparation of Optically Pure (R)-1-[4-(Trifluoromethyl)phenyl]ethanol by Recombinant Whole-Cell-Mediated Reduction

Catalysts ◽  
2019 ◽  
Vol 9 (4) ◽  
pp. 391 ◽  
Author(s):  
Ying Chen ◽  
Nana Xia ◽  
Yuewang Liu ◽  
Pu Wang
Keyword(s):  
Organic Solvent ◽  
Asymmetric Reduction ◽  
Enantiomeric Excess ◽  
Aqueous System ◽  
Cell Membrane Permeability ◽  
Buffer Solution ◽  
Preparative Scale ◽  
Buffer Medium ◽  
Polar Organic Solvent ◽  
Optically Pure

(R)-1-[4-(Trifluoromethyl)phenyl]ethanol is an important pharmaceutical intermediate of a chemokine CCR5 antagonist. In the present study, a bioprocess for the asymmetric reduction of 4-(trifluoromethyl)acetophenone to (R)-1-[4-(trifluoromethyl)phenyl]ethanol was developed by recombinant Escherichia coli cells with excellent enantioselectivity. In order to overcome the conversion limitation performed in the conventional buffer medium resulting from poor solubility of non-natural substrate, we subsequently established a polar organic solvent-aqueous medium to improve the efficacy. Isopropanol was selected as the most suitable cosolvent candidate, based on the investigation on a substrate solubility test and cell membrane permeability assay in different organic solvent-buffer media. Under the optimum conditions, the preparative-scale asymmetric reduction generated a 99.1% yield with >99.9% product enantiomeric excess (ee) in a 15% (v/v) isopropanol proportion, at 100 mM of 4-(trifluoromethyl)acetophenone within 3 h. Compared to bioconversion in the buffer medium, the developed isopropanol-aqueous system enhanced the substrate concentration by 2-fold with a remarkably improved yield (from 62.5% to 99.1%), and shortened the reaction time by 21 h. Our study gave the first example for a highly enantioselective production of (R)-1-[4-(trifluoromethyl)phenyl]ethanol by a biological method, and the bioreduction of 4-(trifluoromethyl)acetophenone in a polar organic solvent-aqueous system was more efficient than that in the buffer solution only. This process is also scalable and has potential in application.

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