Conversion of alcohols to enantiopure amines through dual-enzyme hydrogen-borrowing cascades
α-Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds at industrial scale. We present a biocatalytic hydrogen-borrowing amination of primary and secondary alcohols that allows for the efficient and environmentally benign production of enantiopure amines. The met...
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| Published in | Science (American Association for the Advancement of Science) Vol. 349; no. 6255; pp. 1525 - 1529 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Association for the Advancement of Science
25.09.2015
The American Association for the Advancement of Science |
| Subjects | |
| Online Access | Get full text |
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| Abstract | α-Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds at industrial scale. We present a biocatalytic hydrogen-borrowing amination of primary and secondary alcohols that allows for the efficient and environmentally benign production of enantiopure amines. The method relies on a combination of two enzymes: an alcohol dehydrogenase (from Aromatoleum sp., Lactobacillus sp., or Bacillus sp.) operating in tandem with an amine dehydrogenase (engineered from Bacillus sp.) to aminate a structurally diverse range of aromatic and aliphatic alcohols, yielding up to 96% conversion and 99% enantiomeric excess. Primary alcohols were aminated with high conversion (up to 99%). This redox self-sufficient cascade possesses high atom efficiency, sourcing nitrogen from ammonium and generating water as the sole by-product. |
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| AbstractList | α-Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds at industrial scale. We present a biocatalytic hydrogen-borrowing amination of primary and secondary alcohols that allows for the efficient and environmentally benign production of enantiopure amines. The method relies on a combination of two enzymes: an alcohol dehydrogenase (from Aromatoleum sp., Lactobacillus sp., or Bacillus sp.) operating in tandem with an amine dehydrogenase (engineered from Bacillus sp.) to aminate a structurally diverse range of aromatic and aliphatic alcohols, yielding up to 96% conversion and 99% enantiomeric excess. Primary alcohols were aminated with high conversion (up to 99%). This redox self-sufficient cascade possesses high atom efficiency, sourcing nitrogen from ammonium and generating water as the sole by-product. Enzymes evolved to operate in water and to modify their substrates using comparatively nontoxic reagents. Thus, a major advantage of applying enzymes to synthetic chemistry is their compatibility with environmentally benign conditions. Mutti et al. report that two enzymes--alcohol and amine dehydrogenases--can operate in tandem to convert alcohols to amines. The reaction proceeds with ammonium as the only input and water as the only byproduct. The mechanism relies on consecutive oxidation and reduction steps, with hydrogen shuttled by a nicotinamide coenzyme. Science, this issue p. 1525 α-Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds at industrial scale. We present a biocatalytic hydrogen-borrowing amination of primary and secondary alcohols that allows for the efficient and environmentally benign production of enantiopure amines. The method relies on a combination of two enzymes: an alcohol dehydrogenase (from Aromatoleum sp., Lactobacillus sp., or Bacillus sp.) operating in tandem with an amine dehydrogenase (engineered from Bacillus sp.) to aminate a structurally diverse range of aromatic and aliphatic alcohols, yielding up to 96% conversion and 99% enantiomeric excess. Primary alcohols were aminated with high conversion (up to 99%). This redox self-sufficient cascade possesses high atom efficiency, sourcing nitrogen from ammonium and generating water as the sole by-product. α-Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds on industrial scale. Here we present a biocatalytic hydrogen-borrowing amination of primary and secondary alcohols that allows for the efficient and environmentally benign production of enantiopure amines. The method relies on the combination of an alcohol dehydrogenase (ADHs from Aromatoleum sp., Lactobacillus sp . and Bacillus sp .) enzyme operating in tandem with an amine dehydrogenase (AmDHs engineered from Bacillus sp. ) to aminate a structurally diverse range of aromatic and aliphatic alcohols (up to 96% conversion and 99% enantiomeric excess). Furthermore, primary alcohols are aminated with high conversion (up to 99%). This redox self-sufficient network possesses high atom efficiency, sourcing nitrogen from ammonium and generating water as the sole by-product. A clean and green approach to aminesEnzymes evolved to operate in water and to modify their substrates using comparatively nontoxic reagents. Thus, a major advantage of applying enzymes to synthetic chemistry is their compatibility with environmentally benign conditions. Mutti et al. report that two enzymes-alcohol and amine dehydrogenases-can operate in tandem to convert alcohols to amines. The reaction proceeds with ammonium as the only input and water as the only byproduct. The mechanism relies on consecutive oxidation and reduction steps, with hydrogen shuttled by a nicotinamide coenzyme.Science, this issue p. 1525 alpha -Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds at industrial scale. We present a biocatalytic hydrogen-borrowing amination of primary and secondary alcohols that allows for the efficient and environmentally benign production of enantiopure amines. The method relies on a combination of two enzymes: an alcohol dehydrogenase (from Aromatoleum sp., Lactobacillus sp., or Bacillus sp.) operating in tandem with an amine dehydrogenase (engineered from Bacillus sp.) to aminate a structurally diverse range of aromatic and aliphatic alcohols, yielding up to 96% conversion and 99% enantiomeric excess. Primary alcohols were aminated with high conversion (up to 99%). This redox self-sufficient cascade possesses high atom efficiency, sourcing nitrogen from ammonium and generating water as the sole by-product. A clean and green approach to amines Enzymes evolved to operate in water and to modify their substrates using comparatively nontoxic reagents. Thus, a major advantage of applying enzymes to synthetic chemistry is their compatibility with environmentally benign conditions. Mutti et al. report that two enzymes—alcohol and amine dehydrogenases—can operate in tandem to convert alcohols to amines. The reaction proceeds with ammonium as the only input and water as the only byproduct. The mechanism relies on consecutive oxidation and reduction steps, with hydrogen shuttled by a nicotinamide coenzyme. Science , this issue p. 1525 The pairing of two enzymes offers an environmentally benign protocol for the conversion of alcohols to amines. α-Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds at industrial scale. We present a biocatalytic hydrogen-borrowing amination of primary and secondary alcohols that allows for the efficient and environmentally benign production of enantiopure amines. The method relies on a combination of two enzymes: an alcohol dehydrogenase (from Aromatoleum sp., Lactobacillus sp., or Bacillus sp.) operating in tandem with an amine dehydrogenase (engineered from Bacillus sp.) to aminate a structurally diverse range of aromatic and aliphatic alcohols, yielding up to 96% conversion and 99% enantiomeric excess. Primary alcohols were aminated with high conversion (up to 99%). This redox self-sufficient cascade possesses high atom efficiency, sourcing nitrogen from ammonium and generating water as the sole by-product. |
| Author | Scrutton, Nigel S. Breuer, Michael Turner, Nicholas J. Knaus, Tanja Mutti, Francesco G. |
| AuthorAffiliation | 2 Manchester Institute of Biotechnology, Faculty of Life Sciences, University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK 3 BASF SE, White Biotechnology Research, GBW/B – A030, 67056 Ludwigshafen, Germany 1 School of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, Manchester, M1 7DN, UK |
| AuthorAffiliation_xml | – name: 2 Manchester Institute of Biotechnology, Faculty of Life Sciences, University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK – name: 1 School of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, Manchester, M1 7DN, UK – name: 3 BASF SE, White Biotechnology Research, GBW/B – A030, 67056 Ludwigshafen, Germany |
| Author_xml | – sequence: 1 givenname: Francesco G. surname: Mutti fullname: Mutti, Francesco G. – sequence: 2 givenname: Tanja surname: Knaus fullname: Knaus, Tanja – sequence: 3 givenname: Nigel S. surname: Scrutton fullname: Scrutton, Nigel S. – sequence: 4 givenname: Michael surname: Breuer fullname: Breuer, Michael – sequence: 5 givenname: Nicholas J. surname: Turner fullname: Turner, Nicholas J. |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26404833$$D View this record in MEDLINE/PubMed |
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| ContentType | Journal Article |
| Copyright | Copyright © 2015 American Association for the Advancement of Science Copyright © 2015, American Association for the Advancement of Science. Copyright © 2015, American Association for the Advancement of Science |
| Copyright_xml | – notice: Copyright © 2015 American Association for the Advancement of Science – notice: Copyright © 2015, American Association for the Advancement of Science. – notice: Copyright © 2015, American Association for the Advancement of Science |
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| DOI | 10.1126/science.aac9283 |
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| Snippet | α-Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds at industrial scale. We present a biocatalytic hydrogen-borrowing... A clean and green approach to amines Enzymes evolved to operate in water and to modify their substrates using comparatively nontoxic reagents. Thus, a major... Enzymes evolved to operate in water and to modify their substrates using comparatively nontoxic reagents. Thus, a major advantage of applying enzymes to... A clean and green approach to aminesEnzymes evolved to operate in water and to modify their substrates using comparatively nontoxic reagents. Thus, a major... α-Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds on industrial scale. Here we present a biocatalytic... |
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| SubjectTerms | Alcohol Alcohol Dehydrogenase - chemistry Alcohol Dehydrogenase - genetics Alcohols Alcohols - chemistry Amination Amines Amines - chemical synthesis Bacillus Bacillus - enzymology Bacillus - genetics Biocatalysis Bioengineering Biophysics Byproducts Cascades Chemical engineering Conversion Enzymes Genetic Engineering Hydrogen - chemistry Lactobacillus - enzymology Lactobacillus - genetics Organic Chemistry Oxidoreductases Acting on CH-NH Group Donors - chemistry Oxidoreductases Acting on CH-NH Group Donors - genetics Synthesis (chemistry) Water |
| Title | Conversion of alcohols to enantiopure amines through dual-enzyme hydrogen-borrowing cascades |
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