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

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 med...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2017-06, Vol.19 (12), p.3183-3186
Main Authors: Okada, Masahiro, Saito, Kai, Wong, Chin Piow, Li, Chang, Wang, Dongmei, Iijima, Miu, Taura, Futoshi, Kurosaki, Fumiya, Awakawa, Takayoshi, Abe, Ikuro
Format: Article
Language:English
Subjects:
Chromans - chemistry
Cyclization
Molecular Structure
Rhododendron
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01288