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Area of Science:

  • Biochemistry
  • Enzymology
  • Natural Product Biosynthesis

Background:

  • Thiolactomycin (1) is a promising antibiotic targeting bacterial type II fatty acid synthase.
  • The biosynthesis of its unique gamma-thiolactone ring remains largely unelucidated.
  • Understanding this pathway is crucial for antibiotic development and enzyme engineering.

Purpose of the Study:

  • To elucidate the enzymatic mechanisms responsible for the biosynthesis of the gamma-thiolactone ring in thiolactomycin.
  • To identify the specific enzymes and their roles in this unique natural product formation.

Main Methods:

  • Biochemical assays using purified enzyme domains.
  • Enzyme kinetics and reaction intermediate analysis.
  • Site-directed mutagenesis and in vitro reconstitution experiments.

Main Results:

  • The condensation and heterocyclization (Cy) domain of nonribosomal peptide synthetase TlnC (TlnC_Cy) mediates a novel sulfurtransfer reaction.
  • TlnC_Cy generates a thiocarboxylate intermediate from a polyketide precursor.
  • Cytochrome P450 enzyme TlnA acts as a gamma-thiolactone synthase, catalyzing cyclization via a radical mechanism.

Conclusions:

  • The NRPS TlnC_Cy and P450 TlnA cooperate to assemble the gamma-thiolactone ring of thiolactomycin.
  • This study reveals a unique enzymatic strategy for gamma-thiolactone biosynthesis.
  • Findings expand the known catalytic capabilities of NRPS Cy domains and P450 enzymes.