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Angew Chem Int Ed Engl. 2016 Nov 14;55(47):14823-14827. doi: 10.1002/anie.201607777. Epub 2016 Oct 18.

A One-Pot Cascade Reaction Combining an Encapsulated Decarboxylase with a Metathesis Catalyst for the Synthesis of Bio-Based Antioxidants.

Author information

1
Nachwuchsgruppe für Mikrobielle Biotechnologie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44780, Bochum, Germany.
2
Lehrstuhl für Organische Chemie I, Fakultät für Chemie, Universität Bielefeld, Universitätsstrasse 25, 33615, Bielefeld, Germany.

Abstract

The combination of enzymes with traditional chemical catalysts unifies the high selectivity of the former with the versatility of the latter. A major challenge of this approach is the difference in the optimal reaction conditions for each catalyst type. In this work, we combined a cofactor-free decarboxylase with a ruthenium metathesis catalyst to produce high-value antioxidants from bio-based precursors. As suitable ruthenium catalysts did not show satisfactory activity under aqueous conditions, the reaction required the use of an organic solvent, which in turn significantly reduced enzyme activity. Upon encapsulation of the decarboxylase in a cryogel, the decarboxylation could be conducted in an organic solvent, and the recovery of the enzyme after the reaction was facilitated. After an intermediate drying step, the subsequent metathesis in pure organic solvent proved to be straightforward. The synthetic utility of the cascade was demonstrated by the synthesis of the antioxidant 4,4'-dihydroxystilbene in an overall yield of 90 %.

KEYWORDS:

bio-based antioxidants; biocatalysis; compartmentalization; decarboxylation; metathesis

PMID:
27754591
DOI:
10.1002/anie.201607777

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