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Substrate-Assisted Catalysis in Polyketide Reduction Proceeds via a Phenolate Intermediate.

Martin Schäfer1, Clare E M Stevenson2, Barrie Wilkinson1

  • 1Department of Molecular Microbiology, John Innes Centre, Norwich Research Park, Norwich NR4 7UH, UK.

Cell Chemical Biology
|September 13, 2016
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Summary
This summary is machine-generated.

SimC7, a unique ketoreductase, aids in antibiotic synthesis by reducing a key carbonyl group. Its distinct mechanism involves a substrate-assisted reaction, differing from typical short-chain dehydrogenase/reductase enzymes.

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Enzymology

Background:

  • SimC7 is a polyketide ketoreductase crucial for synthesizing the angucyclinone moiety of simocyclinone D8 (SD8), a gyrase inhibitor.
  • Belonging to the short-chain dehydrogenase/reductase (SDR) superfamily, SimC7 catalyzes the reduction of the C-7 carbonyl, essential for antibiotic activity.

Purpose of the Study:

  • Investigate the distinct catalytic mechanism of SimC7, given its low sequence similarity to other characterized ketoreductases.
  • Elucidate the structural and functional basis for SimC7's unique enzymatic activity.

Main Methods:

  • Determined crystal structures of SimC7 in various states: apo, with NADP(+), and with NADP(+) and substrate (7-oxo-SD8).
  • Performed functional analyses of active-site mutants to probe the reaction mechanism.

Main Results:

  • Structural analysis revealed SimC7 lacks the conserved catalytic triad and active-site tyrosine typical of SDR proteins.
  • Data suggest SimC7 employs a substrate-assisted, two-step reduction mechanism involving intramolecular proton transfer and phenolate intermediate formation.

Conclusions:

  • SimC7 represents a novel class of ketoreductases with a mechanism distinct from canonical SDR enzymes.
  • The identified substrate-assisted mechanism is critical for the biosynthesis of the angucyclinone moiety and the antibiotic activity of simocyclinone D8.