Title |
Biocatalytic site- and enantioselective oxidative dearomatization of phenols
|
---|---|
Published in |
Nature Chemistry, November 2017
|
DOI | 10.1038/nchem.2879 |
Pubmed ID | |
Authors |
Summer A. Baker Dockrey, April L. Lukowski, Marc R. Becker, Alison R. H. Narayan |
Abstract |
The biocatalytic transformations used by chemists are often restricted to simple functional-group interconversions. In contrast, nature has developed complexity-generating biocatalytic reactions within natural product pathways. These sophisticated catalysts are rarely employed by chemists, because the substrate scope, selectivity and robustness of these catalysts are unknown. Our strategy to bridge the gap between the biosynthesis and synthetic chemistry communities leverages the diversity of catalysts available within natural product pathways. Here we show that, starting from a suite of biosynthetic enzymes, catalysts with complementary substrate scope as well as selectivity can be identified. This strategy has been applied to the oxidative dearomatization of phenols, a chemical transformation that rapidly builds molecular complexity from simple starting materials and cannot be accomplished with high selectivity using existing catalytic methods. Using enzymes from biosynthetic pathways, we have successfully developed a method to produce ortho-quinol products with controlled site- and stereoselectivity. Furthermore, we have capitalized on the scalability and robustness of this method in gram-scale reactions as well as multi-enzyme and chemoenzymatic cascades. |
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United Kingdom | 3 | 4% |
Germany | 2 | 3% |
Canada | 2 | 3% |
France | 2 | 3% |
Portugal | 1 | 1% |
Greece | 1 | 1% |
Ecuador | 1 | 1% |
Venezuela, Bolivarian Republic of | 1 | 1% |
Other | 2 | 3% |
Unknown | 22 | 31% |
Demographic breakdown
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Members of the public | 24 | 33% |
Science communicators (journalists, bloggers, editors) | 3 | 4% |
Practitioners (doctors, other healthcare professionals) | 1 | 1% |
Mendeley readers
Geographical breakdown
Country | Count | As % |
---|---|---|
Unknown | 182 | 100% |
Demographic breakdown
Readers by professional status | Count | As % |
---|---|---|
Student > Ph. D. Student | 55 | 30% |
Researcher | 25 | 14% |
Student > Bachelor | 16 | 9% |
Student > Doctoral Student | 11 | 6% |
Student > Master | 10 | 5% |
Other | 27 | 15% |
Unknown | 38 | 21% |
Readers by discipline | Count | As % |
---|---|---|
Chemistry | 108 | 59% |
Biochemistry, Genetics and Molecular Biology | 20 | 11% |
Pharmacology, Toxicology and Pharmaceutical Science | 3 | 2% |
Agricultural and Biological Sciences | 3 | 2% |
Medicine and Dentistry | 3 | 2% |
Other | 3 | 2% |
Unknown | 42 | 23% |