Asymmetric Amination of Secondary Alcohols by using a Redox-Neutral Two-Enzyme Cascade
Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self‐sufficient cascade protocol for the asymmetric amination of racemic secondary alcohols to the corresponding chiral amines was successfully constructed by em...
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| Published in | ChemCatChem Vol. 7; no. 23; pp. 3838 - 3841 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
Blackwell Publishing Ltd
01.12.2015
Wiley Subscription Services, Inc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1867-3880 1867-3899 |
| DOI | 10.1002/cctc.201500785 |
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| Abstract | Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self‐sufficient cascade protocol for the asymmetric amination of racemic secondary alcohols to the corresponding chiral amines was successfully constructed by employing an alcohol dehydrogenase and a newly developed amine dehydrogenase. The compatibility and the identical cofactor dependence of the two enzymes led to an ingenious in situ cofactor recycling system in the one‐pot synthesis. The artificial redox‐neutral cascade process allowed the transformation of racemic secondary alcohols into enantiopure amines with considerable conversions (up to 94 %) and >99 % enantiomeric excess at the expense of only ammonia; this method thus represents a concise and efficient route for the asymmetric synthesis of chiral amines.
If you know what amine: A redox‐neutral two‐enzyme cascade encompassing an alcohol dehydrogenase (ADH) and an amine dehydrogenase (AmDH) is constructed for the synthesis of chiral amines from the corresponding racemic alcohols in one pot to afford considerable conversions (up to 94 %) and high enantiomeric excess values (>99 %) at the expense of only ammonia. |
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| AbstractList | Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self-sufficient cascade protocol for the asymmetric amination of racemic secondary alcohols to the corresponding chiral amines was successfully constructed by employing an alcohol dehydrogenase and a newly developed amine dehydrogenase. The compatibility and the identical cofactor dependence of the two enzymes led to an ingenious insitu cofactor recycling system in the one-pot synthesis. The artificial redox-neutral cascade process allowed the transformation of racemic secondary alcohols into enantiopure amines with considerable conversions (up to 94%) and >99% enantiomeric excess at the expense of only ammonia; this method thus represents a concise and efficient route for the asymmetric synthesis of chiral amines. Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self‐sufficient cascade protocol for the asymmetric amination of racemic secondary alcohols to the corresponding chiral amines was successfully constructed by employing an alcohol dehydrogenase and a newly developed amine dehydrogenase. The compatibility and the identical cofactor dependence of the two enzymes led to an ingenious in situ cofactor recycling system in the one‐pot synthesis. The artificial redox‐neutral cascade process allowed the transformation of racemic secondary alcohols into enantiopure amines with considerable conversions (up to 94 %) and >99 % enantiomeric excess at the expense of only ammonia; this method thus represents a concise and efficient route for the asymmetric synthesis of chiral amines. If you know what amine: A redox‐neutral two‐enzyme cascade encompassing an alcohol dehydrogenase (ADH) and an amine dehydrogenase (AmDH) is constructed for the synthesis of chiral amines from the corresponding racemic alcohols in one pot to afford considerable conversions (up to 94 %) and high enantiomeric excess values (>99 %) at the expense of only ammonia. Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self‐sufficient cascade protocol for the asymmetric amination of racemic secondary alcohols to the corresponding chiral amines was successfully constructed by employing an alcohol dehydrogenase and a newly developed amine dehydrogenase. The compatibility and the identical cofactor dependence of the two enzymes led to an ingenious in situ cofactor recycling system in the one‐pot synthesis. The artificial redox‐neutral cascade process allowed the transformation of racemic secondary alcohols into enantiopure amines with considerable conversions (up to 94 %) and >99 % enantiomeric excess at the expense of only ammonia; this method thus represents a concise and efficient route for the asymmetric synthesis of chiral amines. |
| Author | Zheng, Gao-Wei Liu, You-Yan Chen, Fei-Fei Xu, Jian-He |
| Author_xml | – sequence: 1 givenname: Fei-Fei surname: Chen fullname: Chen, Fei-Fei organization: State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Center for Biomanufacturing, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, P.R. China – sequence: 2 givenname: You-Yan surname: Liu fullname: Liu, You-Yan organization: School of Chemistry and Chemical Engineering, Guangxi University, 530004, Guangxi, Nanning, P.R. China – sequence: 3 givenname: Gao-Wei surname: Zheng fullname: Zheng, Gao-Wei email: gaoweizheng@ecust.edu.cn organization: State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Center for Biomanufacturing, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, P.R. China – sequence: 4 givenname: Jian-He surname: Xu fullname: Xu, Jian-He email: jianhexu@ecust.edu.cn organization: State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Center for Biomanufacturing, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, P.R. China |
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| Copyright | 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Snippet | Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self‐sufficient... Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self-sufficient... |
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| SubjectTerms | amine dehydrogenase asymmetric catalysis biotransformations cascade reaction chiral amines Dehydrogenases |
| Title | Asymmetric Amination of Secondary Alcohols by using a Redox-Neutral Two-Enzyme Cascade |
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