Exploring the Catalytic Promiscuity of Phenolic Acid Decarboxylases: Asymmetric, 1, 6‐Conjugate Addition of Nucleophiles Across 4‐Hydroxystyrene. Issue 12 (8th May 2017)

• Record Type: Journal Article
• Authors: Payer, Stefan E.; Sheng, Xiang; Pollak, Hannah; Wuensch, Christiane; Steinkellner, Georg; Himo, Fahmi; Glueck, Silvia M.; Faber, Kurt
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 12(2017)
• Page Start: 2066
• Page End: 2075
• Publication Date: 2017-05-08
• Subjects: biocatalysis -- catalytic promiscuity -- decarboxylase -- hydration -- hydroxystyrene -- nucleophile addition; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201700247
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The catalytic promiscuity of a ferulic acid decarboxylase from Enterobacter sp. (FDC_ E s) and phenolic acid decarboxylases (PADs) for the asymmetric conjugate addition of water across the C=C bond of hydroxystyrenes was extended to the N‐, C‐ and S‐nucleophiles methoxyamine, cyanide and propanethiol to furnish the corresponding addition products in up to 91% ee . The products obtained from the biotransformation employing the most suitable enzyme/nucleophile pairs were isolated and characterized after optimizing the reaction conditions. Finally, a mechanistic rationale supported by quantum mechanical calculations for the highly ( S )‐selective addition of cyanide is proposed. Abstract :