Promiscuous Oxidosqualene Cyclases from Neoalsomitra integrifoliola Catalyzing the Formation of Tetracyclic, Pentacyclic, and Heterocyclic Triterpenes.

Xiao-Bo Li, Chun-Li Huang, Ying Zhang, Jing-Yang Ding, Gui-Sheng Xiang, Guang-Hui Zhang, Sheng-Chao Yang, Bing Hao

Organic letters 2024 Apr 19

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Six oxidosqualene cyclases (NiOSC1-NiOSC6) from Neoalsomitra integrifoliola were characterized for the biosynthesis of diverse triterpene scaffolds, including tetracyclic and pentacyclic triterpenes from the 2,3-oxidosqualene (1) and oxacyclic triterpenes from the 2,3:22,23-dioxidosqualene (2). NiOSC1 showed high efficiency in the production of naturally rare (20R)-epimers of oxacyclic triterpenes. Mutagenesis results revealed that the NiOSC1-F731G mutant significantly increased the yields of (20R)-epimers compared to the wild type. Homology modeling and molecular docking elucidated the origin of the (20R)-configuration in the epoxide addition step.

Citation

Xiao-Bo Li, Chun-Li Huang, Ying Zhang, Jing-Yang Ding, Gui-Sheng Xiang, Guang-Hui Zhang, Sheng-Chao Yang, Bing Hao. Promiscuous Oxidosqualene Cyclases from Neoalsomitra integrifoliola Catalyzing the Formation of Tetracyclic, Pentacyclic, and Heterocyclic Triterpenes. Organic letters. 2024 Apr 19;26(15):3119-3123