Exploring the Catalytic Promiscuity of Phenolic Acid Decarboxylases: Asymmetric, 1,6-Conjugate Addition of Nucleophiles Across 4-Hydroxystyrene.

Autor: Payer SE; Department of Chemistry University of Graz Heinrichstrasse 28, A-8010 Graz Austria., Sheng X; Arrhenius Laboratory Department of Organic Chemistry Stockholm University SE-106 91 Stockholm Sweden., Pollak H; Department of Chemistry University of Graz Heinrichstrasse 28, A-8010 Graz Austria., Wuensch C; Austrian Centre of Industrial Biotechnology (ACIB) c/o Department of Chemistry University of Graz Heinrichstrasse 28, A-8010 Graz Austria.; Department of Chemistry University of Graz Heinrichstrasse 28, A-8010 Graz Austria., Steinkellner G; Austrian Centre of Industrial Biotechnology (ACIB) c/o Department of Chemistry University of Graz Heinrichstrasse 28, A-8010 Graz Austria.; Center for Molecular Biosciences University of Graz Humboldtstrasse 508010 Graz Austria., Himo F; Arrhenius Laboratory Department of Organic Chemistry Stockholm University SE-106 91 Stockholm Sweden., Glueck SM; Austrian Centre of Industrial Biotechnology (ACIB) c/o Department of Chemistry University of Graz Heinrichstrasse 28, A-8010 Graz Austria.; Department of Chemistry University of Graz Heinrichstrasse 28, A-8010 Graz Austria., Faber K; Department of Chemistry University of Graz Heinrichstrasse 28, A-8010 Graz Austria.
Jazyk: angličtina
Zdroj: Advanced synthesis & catalysis [Adv Synth Catal] 2017 Jun 19; Vol. 359 (12), pp. 2066-2075. Date of Electronic Publication: 2017 May 08.
DOI: 10.1002/adsc.201700247
Abstrakt: 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.
Databáze: MEDLINE
Externí odkaz:
Nepřihlášeným uživatelům se plný text nezobrazuje