Hybrubins: Bipyrrole Tetramic Acids Obtained by Crosstalk between a Truncated Undecylprodigiosin Pathway and Heterologous Tetramic Acid Biosynthetic Genes

Org Lett. 2016 Feb 5;18(3):572-5. doi: 10.1021/acs.orglett.5b03609. Epub 2016 Jan 22.

Abstract

Heterologous expression of bacterial artificial chromosome (BAC) clones from the genomic library of Streptomyces variabilis Snt24 in Streptomyces lividans SBT5 which carried a truncated undecylprodigiosin biosynthetic gene cluster led to the identification of hybrubins A-C. The hybrubins represent a new carbon skeleton in which a tetramic acid moiety is fused to a 2,2'-dipyrrole building block. Gene knockout experiments confirmed that hybrubins are derived from two convergent biosynthetic pathways including the remaining genomic red genes of S. lividans SBT5 as well as the BAC encoded hbn genes for the production of 5-ethylidenetetramic acid. A possible biosynthetic pathway was also proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Molecular Structure
  • Multigene Family
  • Prodigiosin / analogs & derivatives*
  • Prodigiosin / chemistry
  • Pyrrolidinones / chemical synthesis*
  • Pyrrolidinones / chemistry
  • Streptomyces / metabolism

Substances

  • Hydrocarbons, Fluorinated
  • Pyrrolidinones
  • hybrubin A
  • hybrubin B
  • hybrubin C
  • tetramic acid
  • undecylprodigiosin
  • Prodigiosin