Issue 22, 2016

Systems biocatalysis: para-alkenylation of unprotected phenols


Commercially available phenol derivatives were transformed with pyruvate to form a new C–C bond leading to the corresponding para-coumaric acids and only one molecule of water as an innocent side product in buffer. The reaction was catalysed by a biocatalytic system consisting of two enzymatic steps, which were run simultaneously: (i) in the first step catalysed by a tyrosine phenol lyase the C–C coupling of phenol derivatives with pyruvate and ammonia yielded L-tyrosine derivatives, (ii) which were transformed in the second step to the final product via ammonia elimination catalysed by a tyrosine ammonia lyase. The reactions proceeded with exquisite regio- and stereoselectivity yielding just the para-products with the (E)-configuration. The method represents an efficient approach for the direct alkenylation of phenols on a preparative scale (up to 0.6 mmol) affording (E)-para-coumaric acids in excellent isolated yields without requiring chromatographic purification. Co-expression of the involved enzymes in a single host gave access to single catalyst preparation.

Graphical abstract: Systems biocatalysis: para-alkenylation of unprotected phenols

Supplementary files

Article information

Article type
11 Sep 2016
03 Oct 2016
First published
13 Oct 2016
This article is Open Access
Creative Commons BY license

Catal. Sci. Technol., 2016,6, 8098-8103

Systems biocatalysis: para-alkenylation of unprotected phenols

E. Busto, M. Gerstmann, F. Tobola, E. Dittmann, B. Wiltschi and W. Kroutil, Catal. Sci. Technol., 2016, 6, 8098 DOI: 10.1039/C6CY01947A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity