期刊
CATALYSIS SCIENCE & TECHNOLOGY
卷 6, 期 22, 页码 8098-8103出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cy01947a
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资金
- European Commission [FP7-PEOPLE-2011-PIEF-GA-2011-298030]
- Austrian BMWFJ
- BMVIT
- FFG
- SFG
- Standortagentur Tirol
- ZIT through the Austrian FFG-COMET-Funding Program
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.
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