Identification of the product of toxoflavin lyase: degradation via a Baeyer-Villiger oxidation

J Am Chem Soc. 2012 Mar 21;134(11):5326-30. doi: 10.1021/ja211759n. Epub 2012 Mar 9.

Abstract

Toxoflavin (an azapteridine) is degraded to a single product by toxoflavin lyase (TflA) in a reaction dependent on reductant, Mn(II), and oxygen. The isolated product was fully characterized by NMR and MS and was identified as a triazine in which the pyrimidine ring was oxidatively degraded. A mechanism for toxoflavin degradation based on the identification of the enzymatic product and the recently determined crystal structure of toxoflavin lyase is proposed.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Lyases / chemistry
  • Lyases / metabolism*
  • Manganese / chemistry
  • Manganese / metabolism
  • Models, Molecular
  • Molecular Structure
  • Oxidation-Reduction
  • Oxygen / chemistry
  • Oxygen / metabolism
  • Pyrimidinones / chemistry*
  • Pyrimidinones / metabolism
  • Triazines / chemistry*
  • Triazines / metabolism

Substances

  • Pyrimidinones
  • Triazines
  • Manganese
  • toxoflavin
  • Lyases
  • Oxygen