A Photochemoenzymatic Hunsdiecker‐Borodin‐Type Halodecarboxylation of Ferulic Acid. (23rd August 2022)

• Record Type: Journal Article
• Authors: Zippilli, Claudio; Bartolome, Miguel Jimenez; Hilberath, Thomas; Botta, Lorenzo; Hollmann, Frank; Saladino, Raffaele
• Is Part Of: Chembiochem. Volume 23:Number 19(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-23
• Subjects: halodecarboxylation -- phase-transfer catalysis -- photobiocatalysis -- photochemoenzymatic reactions -- vanadium chloroperoxidase; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1002/cbic.202200367
• Languages: English
• ISSNs: 1439-4227

Abstract

Abstract: 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. Abstract : 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.