Cascading Old Yellow Enzyme, Alcohol Dehydrogenase and Glucose Dehydrogenase for Selective Reduction of (<i>E</i>/<i>Z</i>)-Citral to (<i>S</i>)-Citronellol
Citronellol is a kind of unsaturated alcohol with rose-like smell and its (<i>S</i>)-enantiomer serves as an important intermediate for organic synthesis of (-)-<i>cis</i>-rose oxide. Chemical methods are commonly used for the synthesis of citronellol and its (<i>S</...
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2021-07-01
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| Online Access: | https://www.mdpi.com/2073-4344/11/8/931 |
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| author | Yunpeng Jia Qizhou Wang Jingjing Qiao Binbin Feng Xueting Zhou Lijun Jin Yingting Feng Duxia Yang Chenze Lu Xiangxian Ying |
| author_facet | Yunpeng Jia Qizhou Wang Jingjing Qiao Binbin Feng Xueting Zhou Lijun Jin Yingting Feng Duxia Yang Chenze Lu Xiangxian Ying |
| author_sort | Yunpeng Jia |
| collection | DOAJ |
| description | Citronellol is a kind of unsaturated alcohol with rose-like smell and its (<i>S</i>)-enantiomer serves as an important intermediate for organic synthesis of (-)-<i>cis</i>-rose oxide. Chemical methods are commonly used for the synthesis of citronellol and its (<i>S</i>)-enantiomer, which suffers from severe reaction conditions and poor selectivity. Here, the first one-pot double reduction of (<i>E</i>/<i>Z</i>)-citral to (<i>S</i>)-citronellol was achieved in a multi-enzymatic cascade system: N-ethylmaleimide reductase from <i>Providencia stuartii</i> (NemR-PS) was selected to catalyze the selective reduction of (<i>E</i>/<i>Z</i>)-citral to (<i>S</i>)-citronellal, alcohol dehydrogenase from <i>Yokenella</i> sp. WZY002 (YsADH) performed the further reduction of (<i>S</i>)-citronellal to (<i>S</i>)-citronellol, meanwhile a variant of glucose dehydrogenase from <i>Bacillus megaterium</i> (BmGDH<sub>M6</sub>), together with glucose, drove efficient NADPH regeneration. The <i>Escherichia coli</i> strain co-expressing NemR-PS, YsADH, and BmGDH<sub>M6</sub> was successfully constructed and used as the whole-cell catalyst. Various factors were investigated for achieving high conversion and reducing the accumulation of the intermediate (<i>S</i>)-citronellal and by-products. 0.4 mM NADP<sup>+</sup> was essential for maintaining high catalytic activity, while the feeding of the cells expressing BmGDH<sub>M6</sub> effectively eliminated the intermediate and by-products and shortened the reaction time. Under optimized conditions, the bio-transformation of 400 mM citral caused nearly complete conversion (>99.5%) to enantio-pure (<i>S</i>)-citronellol within 36 h, demonstrating promise for industrial application. |
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| institution | Directory Open Access Journal |
| issn | 2073-4344 |
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| spelling | doaj.art-18feb05119e440d3937f6db93f9f4b0a2023-11-22T07:06:53ZengMDPI AGCatalysts2073-43442021-07-0111893110.3390/catal11080931Cascading Old Yellow Enzyme, Alcohol Dehydrogenase and Glucose Dehydrogenase for Selective Reduction of (<i>E</i>/<i>Z</i>)-Citral to (<i>S</i>)-CitronellolYunpeng Jia0Qizhou Wang1Jingjing Qiao2Binbin Feng3Xueting Zhou4Lijun Jin5Yingting Feng6Duxia Yang7Chenze Lu8Xiangxian Ying9Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, ChinaKey Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, ChinaKey Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, ChinaKey Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, ChinaKey Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, ChinaKey Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, ChinaKey Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, ChinaKey Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, ChinaCollege of Life Sciences, China Jiliang University, Hangzhou 310018, ChinaKey Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, ChinaCitronellol is a kind of unsaturated alcohol with rose-like smell and its (<i>S</i>)-enantiomer serves as an important intermediate for organic synthesis of (-)-<i>cis</i>-rose oxide. Chemical methods are commonly used for the synthesis of citronellol and its (<i>S</i>)-enantiomer, which suffers from severe reaction conditions and poor selectivity. Here, the first one-pot double reduction of (<i>E</i>/<i>Z</i>)-citral to (<i>S</i>)-citronellol was achieved in a multi-enzymatic cascade system: N-ethylmaleimide reductase from <i>Providencia stuartii</i> (NemR-PS) was selected to catalyze the selective reduction of (<i>E</i>/<i>Z</i>)-citral to (<i>S</i>)-citronellal, alcohol dehydrogenase from <i>Yokenella</i> sp. WZY002 (YsADH) performed the further reduction of (<i>S</i>)-citronellal to (<i>S</i>)-citronellol, meanwhile a variant of glucose dehydrogenase from <i>Bacillus megaterium</i> (BmGDH<sub>M6</sub>), together with glucose, drove efficient NADPH regeneration. The <i>Escherichia coli</i> strain co-expressing NemR-PS, YsADH, and BmGDH<sub>M6</sub> was successfully constructed and used as the whole-cell catalyst. Various factors were investigated for achieving high conversion and reducing the accumulation of the intermediate (<i>S</i>)-citronellal and by-products. 0.4 mM NADP<sup>+</sup> was essential for maintaining high catalytic activity, while the feeding of the cells expressing BmGDH<sub>M6</sub> effectively eliminated the intermediate and by-products and shortened the reaction time. Under optimized conditions, the bio-transformation of 400 mM citral caused nearly complete conversion (>99.5%) to enantio-pure (<i>S</i>)-citronellol within 36 h, demonstrating promise for industrial application.https://www.mdpi.com/2073-4344/11/8/931old yellow enzymealcohol dehydrogenaseglucose dehydrogenase(<i>E</i>/<i>Z</i>)-citral(<i>S</i>)-citronellolselective reduction |
| spellingShingle | Yunpeng Jia Qizhou Wang Jingjing Qiao Binbin Feng Xueting Zhou Lijun Jin Yingting Feng Duxia Yang Chenze Lu Xiangxian Ying Cascading Old Yellow Enzyme, Alcohol Dehydrogenase and Glucose Dehydrogenase for Selective Reduction of (<i>E</i>/<i>Z</i>)-Citral to (<i>S</i>)-Citronellol Catalysts old yellow enzyme alcohol dehydrogenase glucose dehydrogenase (<i>E</i>/<i>Z</i>)-citral (<i>S</i>)-citronellol selective reduction |
| title | Cascading Old Yellow Enzyme, Alcohol Dehydrogenase and Glucose Dehydrogenase for Selective Reduction of (<i>E</i>/<i>Z</i>)-Citral to (<i>S</i>)-Citronellol |
| title_full | Cascading Old Yellow Enzyme, Alcohol Dehydrogenase and Glucose Dehydrogenase for Selective Reduction of (<i>E</i>/<i>Z</i>)-Citral to (<i>S</i>)-Citronellol |
| title_fullStr | Cascading Old Yellow Enzyme, Alcohol Dehydrogenase and Glucose Dehydrogenase for Selective Reduction of (<i>E</i>/<i>Z</i>)-Citral to (<i>S</i>)-Citronellol |
| title_full_unstemmed | Cascading Old Yellow Enzyme, Alcohol Dehydrogenase and Glucose Dehydrogenase for Selective Reduction of (<i>E</i>/<i>Z</i>)-Citral to (<i>S</i>)-Citronellol |
| title_short | Cascading Old Yellow Enzyme, Alcohol Dehydrogenase and Glucose Dehydrogenase for Selective Reduction of (<i>E</i>/<i>Z</i>)-Citral to (<i>S</i>)-Citronellol |
| title_sort | cascading old yellow enzyme alcohol dehydrogenase and glucose dehydrogenase for selective reduction of i e i i z i citral to i s i citronellol |
| topic | old yellow enzyme alcohol dehydrogenase glucose dehydrogenase (<i>E</i>/<i>Z</i>)-citral (<i>S</i>)-citronellol selective reduction |
| url | https://www.mdpi.com/2073-4344/11/8/931 |
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