On-PKS Baeyer-Villiger-Type O-Atom Insertion Catalyzed by Luciferase-Like Monooxygenase OvmO during Olimycin Biosynthesis

Org Lett. 2020 Mar 6;22(5):1780-1784. doi: 10.1021/acs.orglett.0c00076. Epub 2020 Feb 19.

Abstract

A silent ansamycin biosynthetic gene cluster (ovm) was activated in Streptomyces olivaceus SCSIO T05 following mutagenesis and media optimization. A new shunt product, olimycin C (1a) was produced by the ovmO-inactivated mutant strain, along with a minor product, olimycin D (1b). The production of these linear olimycin counterparts suggest that luciferase-like monooxygenase (LLM) OvmO catalyzes an on-PKS Baeyer-Villiger-type oxidation during assembly of the olimycin A (2) linear polyketide backbone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Lactams, Macrocyclic
  • Luciferases / chemistry
  • Luciferases / genetics
  • Luciferases / metabolism*
  • Mixed Function Oxygenases / chemistry
  • Mixed Function Oxygenases / metabolism*
  • Molecular Structure
  • Multigene Family
  • Oxidation-Reduction
  • Rifabutin / chemistry
  • Rifabutin / metabolism
  • Streptomyces

Substances

  • Lactams, Macrocyclic
  • Rifabutin
  • Mixed Function Oxygenases
  • Luciferases

Supplementary concepts

  • Streptomyces olivaceus