Flavin-enabled reductive and oxidative epoxide ring opening reactions

Bidhan Chandra De, Wenjun Zhang, Chunfang Yang, Attila Mándi, Chunshuai Huang, Liping Zhang, Wei Liu, Mark W. Ruszczycky, Yiguang Zhu, Ming Ma, Ghader Bashiri, Tibor Kurtán, Hung-wen Liu () and Changsheng Zhang ()
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Bidhan Chandra De: Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
Wenjun Zhang: Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
Chunfang Yang: Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
Attila Mándi: University of Debrecen
Chunshuai Huang: Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
Liping Zhang: Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
Wei Liu: Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
Mark W. Ruszczycky: University of Texas at Austin
Yiguang Zhu: Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
Ming Ma: Peking University
Ghader Bashiri: The University of Auckland
Tibor Kurtán: University of Debrecen
Hung-wen Liu: University of Texas at Austin
Changsheng Zhang: Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences

Nature Communications, 2022, vol. 13, issue 1, 1-13

Abstract: Abstract Epoxide ring opening reactions are common and important in both biological processes and synthetic applications and can be catalyzed in a non-redox manner by epoxide hydrolases or reductively by oxidoreductases. Here we report that fluostatins (FSTs), a family of atypical angucyclines with a benzofluorene core, can undergo nonenzyme-catalyzed epoxide ring opening reactions in the presence of flavin adenine dinucleotide (FAD) and nicotinamide adenine dinucleotide (NADH). The 2,3-epoxide ring in FST C is shown to open reductively via a putative enol intermediate, or oxidatively via a peroxylated intermediate with molecular oxygen as the oxidant. These reactions lead to multiple products with different redox states that possess a single hydroxyl group at C-2, a 2,3-vicinal diol, a contracted five-membered A-ring, or an expanded seven-membered A-ring. Similar reactions also take place in both natural products and other organic compounds harboring an epoxide adjacent to a carbonyl group that is conjugated to an aromatic moiety. Our findings extend the repertoire of known flavin chemistry that may provide new and useful tools for organic synthesis.

Date: 2022
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DOI: 10.1038/s41467-022-32641-1

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