Exploring the Catalytic Promiscuity of Phenolic Acid Decarboxylases: Asymmetric, 1,6‐Conjugate Addition of Nucleophiles Across 4‐Hydroxystyrene
Abstract: The catalytic promiscuity of a ferulic acid decarboxylase from Enterobacter sp. (FDC_Es) 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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Exploring the Catalytic Promiscuity of Phenolic Acid Decarboxylases: Asymmetric, 1,6‐Conjugate Addition of Nucleophiles Across 4‐Hydroxystyrene ; volume:359 ; number:12 ; year:2017 ; pages:2066-2075 ; extent:10
Advanced synthesis & catalysis ; 359, Heft 12 (2017), 2066-2075 (gesamt 10)
- Urheber
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Payer, Stefan E.
Sheng, Xiang
Pollak, Hannah
Wuensch, Christiane
Steinkellner, Georg
Himo, Fahmi
Glueck, Silvia M.
Faber, Kurt
- DOI
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10.1002/adsc.201700247
- URN
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urn:nbn:de:101:1-2022091406154869406199
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:22 MESZ
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Beteiligte
- Payer, Stefan E.
- Sheng, Xiang
- Pollak, Hannah
- Wuensch, Christiane
- Steinkellner, Georg
- Himo, Fahmi
- Glueck, Silvia M.
- Faber, Kurt
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