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Regio- and stereodivergent antibiotic oxidative carbocyclizations catalysed by Rieske oxygenase-like enzymes
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Sydor, Paulina K., Barry, Sarah M., Odulate, Olanipekun M., Barona-Gomez, Francisco, Haynes, Stuart W., Corre, Christophe, Song, Lijiang and Challis, Gregory L. (2011) Regio- and stereodivergent antibiotic oxidative carbocyclizations catalysed by Rieske oxygenase-like enzymes. Nature Chemistry, Vol.3 (No.5). pp. 388-392. doi:10.1038/nchem.1024
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Official URL: http://dx.doi.org/10.1038/nchem.1024
Abstract
Oxidative cyclizations, exemplified by the biosynthetic assembly of the penicillin nucleus from a tripeptide precursor, are arguably the most synthetically powerful implementation of C–H activation reactions in nature. Here, we show that Rieske oxygenase-like enzymes mediate regio- and stereodivergent oxidative cyclizations to form 10- and 12-membered carbocyclic rings in the key steps of the biosynthesis of the antibiotics streptorubin B and metacycloprodigiosin, respectively. These reactions represent the first examples of oxidative carbocyclizations catalysed by non-haem iron-dependent oxidases and define a novel type of catalytic activity for Rieske enzymes. A better understanding of how these enzymes achieve such remarkable regio- and stereocontrol in the functionalization of unactivated hydrocarbon chains will greatly facilitate the development of selective man-made C–H activation catalysts.
| Item Type: | Journal Article | ||||
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| Subjects: | Q Science > QD Chemistry Q Science > QP Physiology |
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| Divisions: | Faculty of Science > Chemistry | ||||
| Library of Congress Subject Headings (LCSH): | Catalysis, Enzymes, Biosynthesis, Ring formation (Chemistry) | ||||
| Journal or Publication Title: | Nature Chemistry | ||||
| Publisher: | Nature Publishing Group | ||||
| ISSN: | 1755-4330 | ||||
| Official Date: | 17 April 2011 | ||||
| Dates: |
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| Volume: | Vol.3 | ||||
| Number: | No.5 | ||||
| Page Range: | pp. 388-392 | ||||
| DOI: | 10.1038/nchem.1024 | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access | ||||
| Funder: | University of Warwick, Engineering and Physical Sciences Research Council (EPSRC), National Institutes of Health (U.S.) (NIH), European Union (EU) | ||||
| Grant number: | 1R01GM77147-01A1 (NIH), 005224 (EU) |
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