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

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† Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
‡ Graduate School of Medicine and Pharmaceutical Sciences for Research, University of Toyama, Sugitani, Toyama 930-0194, Japan
*E-mail: [email protected]
*E-mail: [email protected]
Cite this: Org. Lett. 2017, 19, 12, 3183–3186
Publication Date (Web):May 25, 2017
https://doi.org/10.1021/acs.orglett.7b01288
Copyright © 2017 American Chemical Society
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    Abstract

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    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.

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