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Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF‐Amine
Enzymatic enantiopreference is one of the key advantages of biocatalysis. While exploring the synthesis of small cyclic (chiral amines) such as 3‐aminotetrahydrofuran (THF‐amine), using the (S)‐selective transaminase from Halomonas elongata (HEwT), inversion of the enantiopreference was observed at...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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John Wiley and Sons Inc.
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400895/ https://www.ncbi.nlm.nih.gov/pubmed/35705492 http://dx.doi.org/10.1002/cbic.202200335 |
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author | Heckmann, Christian M. Robustini, Lucia Paradisi, Francesca |
author_facet | Heckmann, Christian M. Robustini, Lucia Paradisi, Francesca |
author_sort | Heckmann, Christian M. |
collection | PubMed |
description | Enzymatic enantiopreference is one of the key advantages of biocatalysis. While exploring the synthesis of small cyclic (chiral amines) such as 3‐aminotetrahydrofuran (THF‐amine), using the (S)‐selective transaminase from Halomonas elongata (HEwT), inversion of the enantiopreference was observed at increasing substrate loadings. In addition, the enantiopreference could be altered by variation of the ionic strength, or of the co‐solvent content in the reaction mixture. For example, using otherwise identical reaction conditions, the presence of 2 M sodium chloride gave (R)‐THF‐amine (14 % ee), while the addition of 2.2 M isopropyl alcohol gave the (S)‐enantiomer in 30 % ee. While the underlying cause is not currently understood, it appears likely that subtle changes in the structure of the enzyme cause the shift in enantiopreference and are worth exploring further. |
format | Online Article Text |
id | pubmed-9400895 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-94008952022-08-26 Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF‐Amine Heckmann, Christian M. Robustini, Lucia Paradisi, Francesca Chembiochem Research Articles Enzymatic enantiopreference is one of the key advantages of biocatalysis. While exploring the synthesis of small cyclic (chiral amines) such as 3‐aminotetrahydrofuran (THF‐amine), using the (S)‐selective transaminase from Halomonas elongata (HEwT), inversion of the enantiopreference was observed at increasing substrate loadings. In addition, the enantiopreference could be altered by variation of the ionic strength, or of the co‐solvent content in the reaction mixture. For example, using otherwise identical reaction conditions, the presence of 2 M sodium chloride gave (R)‐THF‐amine (14 % ee), while the addition of 2.2 M isopropyl alcohol gave the (S)‐enantiomer in 30 % ee. While the underlying cause is not currently understood, it appears likely that subtle changes in the structure of the enzyme cause the shift in enantiopreference and are worth exploring further. John Wiley and Sons Inc. 2022-07-01 2022-08-03 /pmc/articles/PMC9400895/ /pubmed/35705492 http://dx.doi.org/10.1002/cbic.202200335 Text en © 2022 The Authors. ChemBioChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Articles Heckmann, Christian M. Robustini, Lucia Paradisi, Francesca Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF‐Amine |
title | Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF‐Amine |
title_full | Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF‐Amine |
title_fullStr | Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF‐Amine |
title_full_unstemmed | Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF‐Amine |
title_short | Influence of Reaction Conditions on Enzymatic Enantiopreference: the Curious Case of HEwT in the Synthesis of THF‐Amine |
title_sort | influence of reaction conditions on enzymatic enantiopreference: the curious case of hewt in the synthesis of thf‐amine |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400895/ https://www.ncbi.nlm.nih.gov/pubmed/35705492 http://dx.doi.org/10.1002/cbic.202200335 |
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