A Photochemoenzymatic Hunsdiecker‐Borodin‐Type Halodecarboxylation of Ferulic Acid

A photochemoenzymatic halodecarboxylation of ferulic acid was achieved using vanadate‐dependent chloroperoxidase as (bio)catalyst and oxygen and organic solvent as sole stoichiometric reagents in a biphasic system. Performance and selectivity were improved through a phase transfer catalyst, reaching...

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Veröffentlicht in:Chembiochem : a European journal of chemical biology 2022-10, Vol.23 (19), p.e202200367-n/a
Hauptverfasser: Zippilli, Claudio, Bartolome, Miguel Jimenez, Hilberath, Thomas, Botta, Lorenzo, Hollmann, Frank, Saladino, Raffaele
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Sprache:eng
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Zusammenfassung:A photochemoenzymatic halodecarboxylation of ferulic acid was achieved using vanadate‐dependent chloroperoxidase as (bio)catalyst and oxygen and organic solvent as sole stoichiometric reagents in a biphasic system. Performance and selectivity were improved through a phase transfer catalyst, reaching a turnover number of 660.000 for the enzyme. Halodecarboxylation of α,β‐unsaturated ferulic acid was achieved by combining photo‐, bio‐ and phase transfer catalysis in a biphasic system. Reactive hypobromite was formed in situ by combining Blue‐LED and vanadium chloroperoxidase, and efficiently transferred from the aqueous to the organic layer by a phase‐transfer catalyst, improving overall performance and selectivity.
ISSN:1439-4227
1439-7633
DOI:10.1002/cbic.202200367