Exploring the Catalytic Promiscuity of Phenolic Acid Decarboxylases: Asymmetric, 1,6-Conjugate Addition of Nucleophiles Across 4-Hydroxystyrene.
Adv Synth Catal
; 359(12): 2066-2075, 2017 06 19.
Article
em En
| MEDLINE
| ID: mdl-28713228
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.
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01-internacional
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MEDLINE
Idioma:
En
Revista:
Adv Synth Catal
Ano de publicação:
2017
Tipo de documento:
Article