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Exploring the Catalytic Promiscuity of Phenolic Acid Decarboxylases: Asymmetric, 1,6-Conjugate Addition of Nucleophiles Across 4-Hydroxystyrene
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 8
2017 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 359, no 12, 2066-2075 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2017. Vol. 359, no 12, 2066-2075 p.
Keyword [en]
biocatalysis, catalytic promiscuity, decarboxylase, hydration, hydroxystyrene, nucleophile addition
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-145208DOI: 10.1002/adsc.201700247ISI: 000403567500006OAI: oai:DiVA.org:su-145208DiVA: diva2:1128909
Available from: 2017-07-31 Created: 2017-07-31 Last updated: 2017-07-31Bibliographically approved

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Sheng, XiangHimo, Fahmi
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