AoiQ Catalyzes Geminal Dichlorination of 1,3-Diketone Natural Products

J Am Chem Soc. 2021 May 19;143(19):7267-7271. doi: 10.1021/jacs.1c02868. Epub 2021 May 6.

Abstract

Enzymes that can perform halogenation of aliphatic carbons are of significant interest to the synthetic and biocatalysis communities. Here we describe the characterization of AoiQ, a single-component flavin-dependent halogenase (FDH) that catalyzes gem-dichlorination of 1,3-diketone substrates in the biosynthesis of dichlorodiaporthin. AoiQ represents the first biochemically reconstituted FDH that can halogenate an enolizable sp3-hybridized carbon atom.

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

  • Biological Products / chemistry
  • Biological Products / metabolism*
  • Flavins / chemistry
  • Flavins / metabolism*
  • Halogenation
  • Ketones / chemistry
  • Ketones / metabolism*
  • Molecular Conformation
  • Oxidoreductases / chemistry
  • Oxidoreductases / metabolism*

Substances

  • Biological Products
  • Flavins
  • Ketones
  • Oxidoreductases