期刊
NATURE CHEMISTRY
卷 3, 期 5, 页码 388-392出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.1024
关键词
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资金
- University of Warwick
- National Institutes of Health [1R01GM77147-01A1]
- Engineering and Physical Sciences Research Council
- European Union [005224]
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.
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