Formation of an Angular Aromatic Polyketide from a Linear Anthrene Precursor via Oxidative Rearrangement

Guixi Gao, Xiangyang Liu, Min Xu, Yemin Wang, Fei Zhang, Lijun Xu, Jin Lv, Qingshan Long, Qianjin Kang, Hong Yu Ou, Ying Wang, Jürgen Rohr, Zixin Deng, Ming Jiang, Shuangjun Lin, Meifeng Tao

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Bacterial aromatic polyketides are a group of natural products synthesized by polyketide synthases (PKSs) that show diverse structures and biological activities. They are structurally subclassified into linear, angular, and discoid aromatic polyketides, the formation of which is commonly determined by the shaping and folding of the poly-β-keto intermediates under the concerted actions of the minimal PKSs, cyclases and ketoreductases. Murayaquinone, found in several streptomycetes, possesses an unusual tricyclic angular aromatic polyketide core containing a 9,10-phenanthraquinone. In this study, genes essential for murayaquinone biosynthesis were identified, and a linear anthraoxirene intermediate was discovered. A unique biosynthetic model for the angular aromatic polyketide formation was discovered and confirmed through in vivo and in vitro studies. Three oxidoreductases, MrqO3, MrqO6, and MrqO7, were identified to catalyze the conversion of the linear aromatic polyketide intermediate into the final angularly arranged framework, which exemplifies a novel strategy for the biosynthesis of angular aromatic polyketides.

Original languageEnglish
Pages (from-to)881-891.e4
JournalCell Chemical Biology
Volume24
Issue number7
DOIs
StatePublished - Jul 20 2017

Bibliographical note

Publisher Copyright:
© 2017 Elsevier Ltd

Keywords

  • Baeyer-Villiger oxygenase
  • angular aromatic polyketides
  • anthracenone epoxide
  • biosynthetic pathway
  • murayaquinone
  • oxidative rearrangement
  • oxidoreductase

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmacology
  • Drug Discovery
  • Clinical Biochemistry

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