Abstract
ABSTRACTThe transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by Pseudomonas fluorescens lipase (PFL) in liquid carbon dioxide (CO2) was reported. Compared with that in organic solvent (n-hexane), the catalytic performance of PFL was dramatically enhanced in liquid CO2. Under the optimal reaction conditions, PFL exhibited an excellent enantioselectivity (E-value: 92.9) with a high enzyme activity (82.5 μmol/g/min). Besides, the remained (S)-3-hydroxy-3-(2-thienyl) propanenitrile with high enantiomeric purity (ee > 99%) was obtained in 4 h when the conversion was about 52%.Lipase-catalyzed transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile in liquid CO2
Highlights
Liu and his coworkers have reported an ultrasound assistant enantioselective transesterification of 3-hydroxy-3-(2thienyl) propanenitrile catalyzed by lipase to increase the catalytic performance of lipase in n-hexane [12]
A low reaction temperature and pressure are beneficial to the catalytic performance of enzyme in liquid CO2
We investigated the effect of water content (0.01–0.06%v/v) on the lipase-catalyzed transesterification in liquid CO2 (Figure 1)
Summary
Duloxetine is a dual inhibitor of serotonin and norepinephrine reuptake and used as an important antidepressant drug [1, 2]. A dynamic kinetic resolution of 3-hydroxy-3-(2-thienyl) propanenitrile using lipase and ruthenium catalyst has been reported by Bäckvall et al to afford (S)-3-hydroxy-3-(2-thienyl) propanenitrile [11] Liu and his coworkers have reported an ultrasound assistant enantioselective transesterification of 3-hydroxy-3-(2thienyl) propanenitrile catalyzed by lipase to increase the catalytic performance of lipase in n-hexane [12]. These reported enzymatic resolutions have encountered some drawbacks, such as low enzyme activity, high temperature and utilization of volatile organic solvents. Some elegant works have been reported that liquid CO2 could effectively enhance lipase activity and enantioselectivity in lipase-catalyzed transesterifications [16–18]. Lipase-catalyzed transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile in liquid CO2 was presented (Scheme 1). To determine the optimal conditions for this lipase-catalyzed reaction, the effect of reaction parameters, such as the type of lipase, acyl donor, water content, substrate molar ratio and enzyme dosage, was studied
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