1. Systems biocatalysis: para-alkenylation of unprotected phenolsElectronic supplementary information (ESI) available. See DOI: 10.1039/c6cy01947a
- Author
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BustoPresent address: Department of Organic Chemistry I, Eduardo, Madrid, Universidad Complutense de, Ma, 28040, Gerstmann, Michaela, Tobola, Felix, Dittmann, Edmund, Wiltschi, Birgit, and Kroutil, Wolfgang
- Abstract
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 viaammonia 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.
- Published
- 2016
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