Combinatorial Biosynthesis of (+)-Daurichromenic Acid and Its Halogenated Analogue

作者：Masahiro Okada, Kai Saito, Chin Piow Wong, Chang Li, Dongmei Wang, Miu Iijima, Futoshi Taura, Fumiya Kurosaki, Takayoshi Awakawa, Ikuro Abe · 发表于：Organic Letters · 年份：2017 · DOI：10.1021/acs.orglett.7b01288 · 被引用次数：32 · 研究领域：Microbial Natural Products and Biosynthesis、Plant biochemistry and biosynthesis、Fungal Biology and Applications

Daurichromenic acid is a meroterpenoid with various pharmacological activities that is biosynthesized from grifolic acid in Rhododendron dauricum. Heterologous expression of grifolic acid synthases from Stachybotrys bisbyi and a daurichromenic acid synthase from R. dauricum in Aspergillus oryzae mediated three-step combinatorial biosynthesis of (+)-daurichromenic acid through enantioselective 6-endo-trig cyclization. Additional introduction of a halogenase from Fusarium sp. into the strain resulted in the biosynthesis of (+)-5-chlorodaurichromenic acid, which exceeds the antibacterial activity of the original compounds.