Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 1, Pages 422-426Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507835
Keywords
4'-methoxyviridicatin; alkaloids; AsqJ dioxygenase; biosynthesis; C-H activation
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Funding
- [1974-01 TUM-KAUST]
- [SFB749]
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Multienzymatic cascades are responsible for the biosynthesis of natural products and represent a source of inspiration for synthetic chemists. The Fe-II/alpha-ketoglutaratedependent dioxygenase AsqJ from Aspergillus nidulans is outstanding because it stereoselectively catalyzes both a ferrylinduced desaturation reaction and epoxidation on a benzodiazepinedione. Interestingly, the enzymatically formed spiro epoxide spring-loads the 6,7-bicyclic skeleton for non-enzymatic rearrangement into the 6,6-bicyclic scaffold of the quinolone alkaloid 4'-methoxyviridicatin. Herein, we report different crystal structures of the protein in the absence and presence of synthesized substrates, surrogates, and intermediates that mimic the various stages of the reaction cycle of this exceptional dioxygenase.
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