Journal
NATURE COMMUNICATIONS
Volume 13, Issue 1, Pages -Publisher
NATURE PORTFOLIO
DOI: 10.1038/s41467-022-32641-1
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Funding
- National Natural Science Foundation of China [31820103003, 42176127, 41676165, 31630004, 31700042]
- Key Science and Technology Project of Hainan Province [ZDKJ202018]
- MOST [2018YFA0901903]
- K.C. Wong Education Foundation [GJTD2020-12]
- Guangdong Provincial Special Fund for Marine Economic Development Project [GDNRC[2021] 48]
- Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) [GML2019ZD0406]
- Youth Innovation Promotion Association CAS [2022349]
- Science and Technology Planning Project of Guangzhou [202102020471]
- CAS-TWAS President's PhD Fellowship
- Welch Foundation [F-1511]
- Sir Charles Hercus Fellowship through the Health Research Council of New Zealand
- National Earth System Data Center, National Science & Technology Infrastructure of China
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Epoxide ring opening reactions are important in both biological processes and synthetic applications. Flavins are shown to catalyze both reductive and oxidative epoxide ring opening reactions, and the underlying mechanisms are proposed.
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. Epoxide ring opening reactions are important in both biological processes and synthetic applications. Here, the authors show that flavin cofactors can catalyze reductive and oxidative epoxide ring opening reactions and propose the underlying mechanisms.
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