Heterologous Reconstitution of Toxoflavin Biosynthesis Reveals Key Pathway Intermediates and a Cofactor-Independent Oxidase

Org Lett. 2023 Apr 28;25(16):2918-2922. doi: 10.1021/acs.orglett.3c01000. Epub 2023 Apr 19.

Abstract

Bacterial azapteridine-containing phytotoxin toxoflavin is a causal agent of rice grain rot. Here, we heterologously reconstitute Bukholderia toxoflavin biosynthesis in Escherichia coli and identify key pathway intermediates, including the hitherto unknown ribityl-dedimethyl-toxoflavin. Furthermore, we characterized a cofactorless oxidase that converts ribityl-dedimethyl-toxoflavin to ribose and dedimethyl-toxoflavin, the latter of which then undergoes stepwise methylations to form toxoflavin. These findings provide new insights into the biosynthetic pathways of toxoflavin and related triazine metabolites.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Oxidoreductases*
  • Pyrimidinones*
  • Triazines

Substances

  • toxoflavin
  • Oxidoreductases
  • Pyrimidinones
  • Triazines