BioLindlar Catalyst: Ene‐Reductase‐Promoted Selective Bioreduction of Cyanoalkynes to Give (Z)‐Cyanoalkenes
Abstract: The direct synthesis of alkenes from alkynes usually requires the use of transition‐metal catalysts. Unfortunately, efficient biocatalytic alternatives for this transformation have yet to be discovered. Herein, the selective bioreduction of electron‐deficient alkynes to alkenes catalysed by ene‐reductases (EREDs) is described. Alkynes bearing ketone, aldehyde, ester, and nitrile moieties have been effectively reduced with excellent conversions and stereoselectivities, observing clear trends for the E/Z ratios depending on the nature of the electron‐withdrawing group. In the case of cyanoalkynes, (Z)‐alkenes were obtained as the major product, and the reaction scope was expanded to a wide variety of aromatic substrates (up to >99 % conversion, and Z/E stereoselectivities of up to >99/1). Other alkynes containing aldehyde, ketone, or ester functionalities also proved to be excellent substrates, and interestingly gave the corresponding (E)‐alkenes. Preparative biotransformations were performed on a 0.4 mmol scale, producing the desired (Z)‐cyanoalkenes with good to excellent isolated yields (63–97 %). This novel reactivity has been rationalised through molecular docking by predicting the binding poses of key molecules in the ERED‐pu‐0006 active site.
- 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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BioLindlar Catalyst: Ene‐Reductase‐Promoted Selective Bioreduction of Cyanoalkynes to Give (Z)‐Cyanoalkenes ; day:20 ; month:08 ; year:2024 ; extent:9
Angewandte Chemie ; (20.08.2024) (gesamt 9)
- Creator
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González‐Rodríguez, Jorge
González‐Granda, Sergio
Kumar, Hirdesh
Alvizo, Oscar
Escot, Lorena
Hailes, Helen C.
Gotor‐Fernández, Vicente
Lavandera, Iván
- DOI
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10.1002/ange.202410283
- URN
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urn:nbn:de:101:1-2408211414029.991568637438
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:46 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- González‐Rodríguez, Jorge
- González‐Granda, Sergio
- Kumar, Hirdesh
- Alvizo, Oscar
- Escot, Lorena
- Hailes, Helen C.
- Gotor‐Fernández, Vicente
- Lavandera, Iván
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BioLindlar Catalyst: Ene‐Reductase‐Promoted Selective Bioreduction of Cyanoalkynes to Give (Z)‐Cyanoalkenes
Ene‐Reductase‐Catalyzed Oxidation Reactions
Purple‐Light Promoted Thiol‐ene Reaction of Alkenes
Rhodococcus strains as source for ene-reductase activity
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Selective ene‐reductase immobilization to magnetic nanoparticles through a novel affinity tag
Ene‐Reductase Catalyzed Regio‐ and Stereoselective 1,4‐Mono‐Reduction of Pseudoionone to Geranylacetone
Studies on variable surface loop regions of the ene reductase NCR from Zymomonas mobilis
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BioLindlar Catalyst: Ene‐Reductase‐Promoted Selective Bioreduction of Cyanoalkynes to Give (Z)‐Cyanoalkenes
Ene‐Reductase‐Catalyzed Oxidation Reactions
Purple‐Light Promoted Thiol‐ene Reaction of Alkenes
Rhodococcus strains as source for ene-reductase activity
Give, give
Selective ene‐reductase immobilization to magnetic nanoparticles through a novel affinity tag
Ene‐Reductase Catalyzed Regio‐ and Stereoselective 1,4‐Mono‐Reduction of Pseudoionone to Geranylacetone
Studies on variable surface loop regions of the ene reductase NCR from Zymomonas mobilis
Asymmetric Reduction of (R)‐Carvone through a Thermostable and Organic‐Solvent‐Tolerant Ene‐Reductase
Ene-Reductase Permits Cross-Electrophile Coupling of α-Chloro Carbonyls with α-Aryl Nitroalkanes
Asymmetric reduction of (R)‐carvone through a thermostable and organic‐solvent‐tolerant ene‐reductase