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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]

PMID: 27960349

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