Organic Letters
Organic Letters
5 years ago

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

Combinatorial Biosynthesis of (+)-Daurichromenic Acid and Its Halogenated Analogue
Fumiya Kurosaki, Masahiro Okada, Futoshi Taura, Dongmei Wang, Miu Iijima, Kai Saito, Ikuro Abe, Chin Piow Wong, Takayoshi Awakawa, Chang Li
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01288

DOI: 10.1021/acs.orglett.7b01288

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