Stereochemical Control of Enzymatic Carbon–Carbon Bond‐Forming Michael‐Type Additions by “Substrate Engineering”
The enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously catalyzes the Michael‐type addition of acetaldehyde to β‐nitrostyrene derivatives to yield chiral γ‐nitroaldehydes, which are important precursors for pharmaceutically active γ‐aminobutyric acids. In this study, we investigated the effect of different substituents at the aromatic ring of the Michael acceptor on the catalytic efficiency and stereoselectivity of the 4‐OT‐catalyzed acetaldehyde addition reactions. Highly enantioenriched (R)‐ and (S)‐γ‐nitroaldehydes and 4‐substituted chroman‐2‐ol could be obtained in good to excellent yields by applying different substituents at appropriate positions of the aromatic substrate. Stereochemical control of these enzymatic Michael‐type additions by “substrate engineering” allowed the enantioselective synthesis of valuable γ‐aminobutyric acid precursors. In addition, the results suggest a novel enzymatic synthesis route towards precursors for chromans and derivatives, which are valuable scaffolds for preparing biologically active natural products.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Stereochemical Control of Enzymatic Carbon–Carbon Bond‐Forming Michael‐Type Additions by “Substrate Engineering” ; volume:2016 ; number:32 ; year:2016 ; pages:5350-5354 ; extent:5
European journal of organic chemistry ; 2016, Heft 32 (2016), 5350-5354 (gesamt 5)
- Creator
- DOI
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10.1002/ejoc.201601126
- URN
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urn:nbn:de:101:1-2022111006461271617662
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
- 15.08.2025, 7:38 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Miao, Yufeng
- Tepper, Pieter G.
- Geertsema, Edzard M.
- Poelarends, Gerrit
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