Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 47, Pages 12880-12884Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407920
Keywords
alkaloids; enzymes; gene expression; natural products; oxidations
Categories
Funding
- Japan Society for the Promotion of Science (JSPS) through Funding Program for Next Generation World-Leading Researchers
- Council for Science and Technology Policy [LS103]
- Industrial Technology Research Grant Program, New Energy and Industrial Technology Development Organization (NEDO) of Japan [09C46001a]
- Amano Enzyme Foundation
- Mochida Memorial Foundation for Medical and Pharmaceutical Research
- The Naito Foundation Japan
- Nagase Science and Technology Foundation Japan
- Takeda Science Foundation
- National Institute of General Medical Sciences [PO1-GM084077]
- National Science Foundation, Emerging Frontiers in Research and Innovation MIKS grant [1136903]
- Grants-in-Aid for Scientific Research [23406031] Funding Source: KAKEN
- Emerging Frontiers & Multidisciplinary Activities
- Directorate For Engineering [1136903] Funding Source: National Science Foundation
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The 6,6-quinolone scaffold of the viridicatin-type of fungal alkaloids are found in various quinolone alkaloids which often exhibit useful biological activities. Thus, it is of interest to identify viridicatin-forming enzymes and understand how such alkaloids are biosynthesized. Here an Aspergillal gene cluster responsible for the biosynthesis of 4'-methoxyviridicatin was identified. Detailed in vitro studies led to the discovery of the dioxygenase AsqJ which performs two distinct oxidations: first desaturation to form a double bond and then monooxygenation of the double bond to install an epoxide. Interestingly, the epoxidation promotes non-enzymatic rear-rangement of the 6,7-bicyclic core of 4'-methoxycyclopenin into the 6,6-quinolone viridicatin scaffold to yield 4'-methoxyviridicatin. The finding provides new insight into the biosynthesis of the viridicatin scaffold and suggests dioxygenase as a potential tool for 6,6-quinolone synthesis by epoxidation of benzodiazepinediones.
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