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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 ISSN 1755-4330.

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Official URL: http://dx.doi.org/10.1038/nchem.1024

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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
Subjects: Q Science > QD Chemistry
Q Science > QP Physiology
Divisions: Faculty of Science, Engineering and Medicine > 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:
DateEvent
17 April 2011Published
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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