Efficient 1-Hydroxy-2-Butanone Production from 1,2-Butanediol by Whole Cells of Engineered <i>E. coli</i>
1-Hydroxy-2-butanone (HB) is a key intermediate for anti-tuberculosis pharmaceutical ethambutol. Commercially available HB is primarily obtained by the oxidation of 1,2-butanediol (1,2-BD) using chemical catalysts. In present study, seven enzymes including diol dehydrogenases, secondary alcohol dehy...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-09-01
|
| Series: | Catalysts |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4344/11/10/1184 |
| _version_ | 1797515103420022784 |
|---|---|
| author | Hui Lin Jiayin Xu Wenlian Sun Wujia Hu Huifang Gao Kaihui Hu Junzhi Qiu Binbin Huang Liaoyuan Zhang |
| author_facet | Hui Lin Jiayin Xu Wenlian Sun Wujia Hu Huifang Gao Kaihui Hu Junzhi Qiu Binbin Huang Liaoyuan Zhang |
| author_sort | Hui Lin |
| collection | DOAJ |
| description | 1-Hydroxy-2-butanone (HB) is a key intermediate for anti-tuberculosis pharmaceutical ethambutol. Commercially available HB is primarily obtained by the oxidation of 1,2-butanediol (1,2-BD) using chemical catalysts. In present study, seven enzymes including diol dehydrogenases, secondary alcohol dehydrogenases and glycerol dehydrogenase were chosen to evaluate their abilities in the conversion of 1,2-BD to HB. The results showed that (2<i>R</i>, 3<i>R</i>)- and (2<i>S</i>, 3<i>S</i>)-butanediol dehydrogenase (BDH) from <i>Serratia</i> sp. T241 could efficiently transform (<i>R</i>)- and (<i>S</i>)-1,2-BD into HB respectively. Furthermore, two biocatalysts co-expressing (2<i>R</i>, 3<i>R</i>)-/(2<i>S</i>, 3<i>S</i>)-BDH, NADH oxidase and hemoglobin protein in <i>Escherichia coli</i> were developed to convert 1,2-BD mixture into HB, and the transformation conditions were optimized. Maximum HB yield of 341.35 and 188.80 mM could be achieved from 440 mM (<i>R</i>)-1,2-BD and 360 mM (<i>S</i>)-1,2-BD by <i>E. coli</i> (pET-<i>rrbdh</i>-<i>nox</i>-<i>vgb</i>) and <i>E. coli</i> (pET-<i>ssbdh</i>-<i>nox</i>-<i>vgb</i>) under the optimized conditions. In addition, two biocatalysts showed the ability in chiral resolution of 1,2-BD isomers, and 135.68 mM (<i>S</i>)-1,2-BD and 112.43 mM (<i>R</i>)-1,2-BD with the purity of 100% could be obtained from 300 and 200 mM 1,2-BD mixture by <i>E. coli</i> (pET-<i>rrbdh</i>-<i>nox</i>-<i>vgb</i>) and <i>E. coli</i> (pET-<i>ssbdh</i>-<i>nox</i>-<i>vgb</i>), respectively. These results provided potential application for HB production from 1,2-BD mixture and chiral resolution of (<i>R</i>)-1,2-BD and (<i>S</i>)-1,2-BD. |
| first_indexed | 2024-03-10T06:40:52Z |
| format | Article |
| id | doaj.art-cff4ab379e2c441a9699f76fd62c018b |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T06:40:52Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-cff4ab379e2c441a9699f76fd62c018b2023-11-22T17:43:30ZengMDPI AGCatalysts2073-43442021-09-011110118410.3390/catal11101184Efficient 1-Hydroxy-2-Butanone Production from 1,2-Butanediol by Whole Cells of Engineered <i>E. coli</i>Hui Lin0Jiayin Xu1Wenlian Sun2Wujia Hu3Huifang Gao4Kaihui Hu5Junzhi Qiu6Binbin Huang7Liaoyuan Zhang8Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Life Sciences, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaDepartment of Pharmacy, The First Affiliated Hospital of Xiamen University, Xiamen 361022, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Life Sciences, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Life Sciences, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Life Sciences, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Life Sciences, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Life Sciences, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaCollege of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Life Sciences, Fujian Agriculture and Forestry University, Fuzhou 350002, China1-Hydroxy-2-butanone (HB) is a key intermediate for anti-tuberculosis pharmaceutical ethambutol. Commercially available HB is primarily obtained by the oxidation of 1,2-butanediol (1,2-BD) using chemical catalysts. In present study, seven enzymes including diol dehydrogenases, secondary alcohol dehydrogenases and glycerol dehydrogenase were chosen to evaluate their abilities in the conversion of 1,2-BD to HB. The results showed that (2<i>R</i>, 3<i>R</i>)- and (2<i>S</i>, 3<i>S</i>)-butanediol dehydrogenase (BDH) from <i>Serratia</i> sp. T241 could efficiently transform (<i>R</i>)- and (<i>S</i>)-1,2-BD into HB respectively. Furthermore, two biocatalysts co-expressing (2<i>R</i>, 3<i>R</i>)-/(2<i>S</i>, 3<i>S</i>)-BDH, NADH oxidase and hemoglobin protein in <i>Escherichia coli</i> were developed to convert 1,2-BD mixture into HB, and the transformation conditions were optimized. Maximum HB yield of 341.35 and 188.80 mM could be achieved from 440 mM (<i>R</i>)-1,2-BD and 360 mM (<i>S</i>)-1,2-BD by <i>E. coli</i> (pET-<i>rrbdh</i>-<i>nox</i>-<i>vgb</i>) and <i>E. coli</i> (pET-<i>ssbdh</i>-<i>nox</i>-<i>vgb</i>) under the optimized conditions. In addition, two biocatalysts showed the ability in chiral resolution of 1,2-BD isomers, and 135.68 mM (<i>S</i>)-1,2-BD and 112.43 mM (<i>R</i>)-1,2-BD with the purity of 100% could be obtained from 300 and 200 mM 1,2-BD mixture by <i>E. coli</i> (pET-<i>rrbdh</i>-<i>nox</i>-<i>vgb</i>) and <i>E. coli</i> (pET-<i>ssbdh</i>-<i>nox</i>-<i>vgb</i>), respectively. These results provided potential application for HB production from 1,2-BD mixture and chiral resolution of (<i>R</i>)-1,2-BD and (<i>S</i>)-1,2-BD.https://www.mdpi.com/2073-4344/11/10/11841-hydroxy-2-butanone1,2-butanedioldiol dehydrogenasewhole cell biocatalysischiral resolution |
| spellingShingle | Hui Lin Jiayin Xu Wenlian Sun Wujia Hu Huifang Gao Kaihui Hu Junzhi Qiu Binbin Huang Liaoyuan Zhang Efficient 1-Hydroxy-2-Butanone Production from 1,2-Butanediol by Whole Cells of Engineered <i>E. coli</i> Catalysts 1-hydroxy-2-butanone 1,2-butanediol diol dehydrogenase whole cell biocatalysis chiral resolution |
| title | Efficient 1-Hydroxy-2-Butanone Production from 1,2-Butanediol by Whole Cells of Engineered <i>E. coli</i> |
| title_full | Efficient 1-Hydroxy-2-Butanone Production from 1,2-Butanediol by Whole Cells of Engineered <i>E. coli</i> |
| title_fullStr | Efficient 1-Hydroxy-2-Butanone Production from 1,2-Butanediol by Whole Cells of Engineered <i>E. coli</i> |
| title_full_unstemmed | Efficient 1-Hydroxy-2-Butanone Production from 1,2-Butanediol by Whole Cells of Engineered <i>E. coli</i> |
| title_short | Efficient 1-Hydroxy-2-Butanone Production from 1,2-Butanediol by Whole Cells of Engineered <i>E. coli</i> |
| title_sort | efficient 1 hydroxy 2 butanone production from 1 2 butanediol by whole cells of engineered i e coli i |
| topic | 1-hydroxy-2-butanone 1,2-butanediol diol dehydrogenase whole cell biocatalysis chiral resolution |
| url | https://www.mdpi.com/2073-4344/11/10/1184 |
| work_keys_str_mv | AT huilin efficient1hydroxy2butanoneproductionfrom12butanediolbywholecellsofengineerediecolii AT jiayinxu efficient1hydroxy2butanoneproductionfrom12butanediolbywholecellsofengineerediecolii AT wenliansun efficient1hydroxy2butanoneproductionfrom12butanediolbywholecellsofengineerediecolii AT wujiahu efficient1hydroxy2butanoneproductionfrom12butanediolbywholecellsofengineerediecolii AT huifanggao efficient1hydroxy2butanoneproductionfrom12butanediolbywholecellsofengineerediecolii AT kaihuihu efficient1hydroxy2butanoneproductionfrom12butanediolbywholecellsofengineerediecolii AT junzhiqiu efficient1hydroxy2butanoneproductionfrom12butanediolbywholecellsofengineerediecolii AT binbinhuang efficient1hydroxy2butanoneproductionfrom12butanediolbywholecellsofengineerediecolii AT liaoyuanzhang efficient1hydroxy2butanoneproductionfrom12butanediolbywholecellsofengineerediecolii |