Ultrasound promoted enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by lipase
(S)-3-hydroxy-3-(2-thienyl) propanenitrile, which is the key chiral building block for the synthesis of (S)-duloxetine, was successfully prepared via enantioselective transesterification catalyzed by lipase under ultrasound irradiation. Compared with conventional shaking, the enzyme activity and ena...
Main Authors: | , , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
Taylor & Francis Group
2016-10-01
|
Series: | Green Chemistry Letters and Reviews |
Subjects: | |
Online Access: | http://dx.doi.org/10.1080/17518253.2016.1216611 |
id |
doaj-bb522e24db0648268fa19097fcd9daae |
---|---|
record_format |
Article |
spelling |
doaj-bb522e24db0648268fa19097fcd9daae2020-11-24T23:26:37ZengTaylor & Francis GroupGreen Chemistry Letters and Reviews1751-82531751-71922016-10-019419019510.1080/17518253.2016.12166111216611Ultrasound promoted enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by lipaseShuyin Liu0Guihua Xiong1JinLiang Gao2Fengxi Li3Shushu Wei4Zhi Wang5Lei Wang6Changchun University of Chinese MedicineChangchun University of Chinese MedicineChangchun University of Chinese MedicineJilin UniversityJilin UniversityJilin UniversityJilin University(S)-3-hydroxy-3-(2-thienyl) propanenitrile, which is the key chiral building block for the synthesis of (S)-duloxetine, was successfully prepared via enantioselective transesterification catalyzed by lipase under ultrasound irradiation. Compared with conventional shaking, the enzyme activity and enantioselectivity were dramatically enhanced under ultrasound irradiation. Under optimum reaction conditions (solvent: n-hexane, ultrasound power: 150 W, aw: 0.33, temperature: 40°C), Pseudomonas sp. lipase exhibited an excellent catalytic performance (enzyme activity: 81.5 μmol g−1 min−1, E-value: 65.4). The reaction achieved its equilibrium in approximately 7 h with a conversion of 53.9% and high enantiopurity (99% ee) of (S)-3-hydroxy-3-(2-thienyl) propanenitrile could be obtained.http://dx.doi.org/10.1080/17518253.2016.12166113-Hydroxy-3-(2-thienyl) propanenitrilelipaseresolutionultrasound |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Shuyin Liu Guihua Xiong JinLiang Gao Fengxi Li Shushu Wei Zhi Wang Lei Wang |
spellingShingle |
Shuyin Liu Guihua Xiong JinLiang Gao Fengxi Li Shushu Wei Zhi Wang Lei Wang Ultrasound promoted enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by lipase Green Chemistry Letters and Reviews 3-Hydroxy-3-(2-thienyl) propanenitrile lipase resolution ultrasound |
author_facet |
Shuyin Liu Guihua Xiong JinLiang Gao Fengxi Li Shushu Wei Zhi Wang Lei Wang |
author_sort |
Shuyin Liu |
title |
Ultrasound promoted enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by lipase |
title_short |
Ultrasound promoted enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by lipase |
title_full |
Ultrasound promoted enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by lipase |
title_fullStr |
Ultrasound promoted enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by lipase |
title_full_unstemmed |
Ultrasound promoted enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by lipase |
title_sort |
ultrasound promoted enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile catalyzed by lipase |
publisher |
Taylor & Francis Group |
series |
Green Chemistry Letters and Reviews |
issn |
1751-8253 1751-7192 |
publishDate |
2016-10-01 |
description |
(S)-3-hydroxy-3-(2-thienyl) propanenitrile, which is the key chiral building block for the synthesis of (S)-duloxetine, was successfully prepared via enantioselective transesterification catalyzed by lipase under ultrasound irradiation. Compared with conventional shaking, the enzyme activity and enantioselectivity were dramatically enhanced under ultrasound irradiation. Under optimum reaction conditions (solvent: n-hexane, ultrasound power: 150 W, aw: 0.33, temperature: 40°C), Pseudomonas sp. lipase exhibited an excellent catalytic performance (enzyme activity: 81.5 μmol g−1 min−1, E-value: 65.4). The reaction achieved its equilibrium in approximately 7 h with a conversion of 53.9% and high enantiopurity (99% ee) of (S)-3-hydroxy-3-(2-thienyl) propanenitrile could be obtained. |
topic |
3-Hydroxy-3-(2-thienyl) propanenitrile lipase resolution ultrasound |
url |
http://dx.doi.org/10.1080/17518253.2016.1216611 |
work_keys_str_mv |
AT shuyinliu ultrasoundpromotedenantioselectivetransesterificationof3hydroxy32thienylpropanenitrilecatalyzedbylipase AT guihuaxiong ultrasoundpromotedenantioselectivetransesterificationof3hydroxy32thienylpropanenitrilecatalyzedbylipase AT jinlianggao ultrasoundpromotedenantioselectivetransesterificationof3hydroxy32thienylpropanenitrilecatalyzedbylipase AT fengxili ultrasoundpromotedenantioselectivetransesterificationof3hydroxy32thienylpropanenitrilecatalyzedbylipase AT shushuwei ultrasoundpromotedenantioselectivetransesterificationof3hydroxy32thienylpropanenitrilecatalyzedbylipase AT zhiwang ultrasoundpromotedenantioselectivetransesterificationof3hydroxy32thienylpropanenitrilecatalyzedbylipase AT leiwang ultrasoundpromotedenantioselectivetransesterificationof3hydroxy32thienylpropanenitrilecatalyzedbylipase |
_version_ |
1725554267985543168 |