Identification of NanE as the thioesterase for polyether chain release in nanchangmycin biosynthesis

Chem Biol. 2006 Sep;13(9):945-55. doi: 10.1016/j.chembiol.2006.07.006.

Abstract

The polyketide synthase (PKS) for the biosynthesis of the polyether nanchangmycin lacks an apparent thioesterase comparable to the type I thioesterase domains of the modular PKSs responsible for macrolide biosynthesis. Three candidate polyether chain-releasing factors were examined. Both the putative CR domain and the NanE protein appeared to be genetically relevant. Among the three heterologously expressed soluble proteins (recombinant CR domain, the ACP-CR didomain, and NanE) tested, only NanE hydrolyzed the polyether-SNAC. By contrast, recombinant DEBS TE from the erythromycin pathway, and the recombinant MonAX, a type II TE associated with the polyether monensin biosynthesis for which a homolog has not been detected in the nanchangmycin cluster, hydrolyzed a diketide-SNAC but not the polyether-SNAC. We could thus conclude that NanE is a dedicated thioesterase mediating the specific release of the polyether chain during nanchangmycin biosynthesis.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Chromatography, Liquid
  • Ethers / chemistry
  • Ethers / metabolism*
  • Gene Deletion
  • Mass Spectrometry
  • Molecular Sequence Data
  • Mutation
  • Phylogeny
  • Polyketide Synthases / chemistry*
  • Polyketide Synthases / metabolism
  • Protein Structure, Tertiary
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / metabolism
  • Sequence Alignment
  • Spiro Compounds / chemistry
  • Spiro Compounds / metabolism*
  • Streptomyces / enzymology*
  • Streptomyces / genetics
  • Thiolester Hydrolases / chemistry*
  • Thiolester Hydrolases / metabolism*

Substances

  • Ethers
  • Recombinant Proteins
  • Spiro Compounds
  • nanchangmycin
  • Polyketide Synthases
  • Thiolester Hydrolases