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Biochemical Characterization of a Eukaryotic Decalin-Forming Diels-Alderase.

ABSTRACT: 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.

SUBMITTER: Li L 

PROVIDER: S-EPMC5323083 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Biochemical Characterization of a Eukaryotic Decalin-Forming Diels-Alderase.

Li Li L   Yu Peiyuan P   Tang Man-Cheng MC   Zou Yi Y   Gao Shu-Shan SS   Hung Yiu-Sun YS   Zhao Muxun M   Watanabe Kenji K   Houk K N KN   Tang Yi Y  

Journal of the American Chemical Society 20161130 49

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. ...[more]