Journal
CHEMBIOCHEM
Volume 15, Issue 2, Pages 284-292Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201300626
Keywords
flavin-dependent halogenases; natural products; oxidative coupling reaction; Pestalotiopsis fici; pestheic acid biosynthesis
Funding
- Ministry of Science and Technology of China [2012ZX09301-003]
- National Natural Science Foundation of China [31030003, 30925039, 21372004]
- Chinese Academy of Sciences [KSCX2-EW-J-6]
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The diphenyl ether pestheic acid was isolated from the endophytic fungus Pestalotiopsis fici, which is proposed to be the biosynthetic precursor of the unique chloropupukeananes. The pestheic acid biosynthetic gene (pta) cluster was identified in the fungus through genome scanning. Sequence analysis revealed that this gene cluster encodes a nonreducing polyketide synthase, a number of modification enzymes, and three regulators. Gene disruption and intermediate analysis demonstrated that the biosynthesis proceeded through formation of the polyketide backbone, cyclization of a polyketo acid to a benzophenone, chlorination, and formation of the diphenyl ether skeleton through oxidation and hydrolyzation. A dihydrogeodin oxidase gene, ptaE, was essential for diphenyl ether formation, and ptaM encoded a flavin-dependent halogenase catalyzing chlorination in the biosynthesis. Identification of the pta cluster laid the foundation to decipher the genetic and biochemical mechanisms involved in the pathway.
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