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Biochemical Characterization of a Eukaryotic Decalin-Forming Diels–Alderase
- Li, Li, Yu, Peiyuan, Tang, Man-Cheng, Zou, Yi, Gao, Shu-Shan, Hung, Yiu-Sun, Zhao, Muxun, Watanabe, Kenji, Houk, K. N., Tang, Yi
- Journal of the American Chemical Society 2016 v.138 no.49 pp. 15837-15840
- biochemical pathways, cycloaddition reactions, cytotoxicity, fungi, stereochemistry
- The trans-decalin structure formed by intramolecular Diels–Alder cycloaddition is widely present among bioactive natural products isolated from fungi. We elucidated the concise three-enzyme biosynthetic pathway of the cytotoxic myceliothermophin and biochemically characterized the Diels–Alderase that catalyzes the formation of trans-decalin from an acyclic substrate. Computational studies of the reaction mechanism rationalize both the substrate and stereoselectivity of the enzyme.