Heckmann, Christian M; Robustini, Lucia; Paradisi, Francesca (2022). Influence of reaction conditions on enzymatic enantiopreference: the curious case of HEwT in the synthesis of THF-amine. ChemBioChem, 23(15), e202200335. Wiley 10.1002/cbic.202200335
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ChemBioChem_-_2022_-_Heckmann_-_Influence_of_reaction_conditions_on_enzymatic_enantiopreference_the_curious_case_of_HEwT.pdf - Accepted Version Available under License Publisher holds Copyright. Download (3MB) | Preview |
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 also 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.
Item Type: |
Journal Article (Original Article) |
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Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Robustini, Lucia, Paradisi, Francesca |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
1439-7633 |
Publisher: |
Wiley |
Language: |
English |
Submitter: |
Pubmed Import |
Date Deposited: |
22 Jun 2022 12:53 |
Last Modified: |
17 Jun 2023 00:25 |
Publisher DOI: |
10.1002/cbic.202200335 |
PubMed ID: |
35705492 |
Uncontrolled Keywords: |
Biocatalysis THF-amine Trasaminases additive effect enantiopreference |
BORIS DOI: |
10.48350/170777 |
URI: |
https://boris.unibe.ch/id/eprint/170777 |
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