Prenylated flavins: structures and mechanisms

FEBS J. 2023 May;290(9):2232-2245. doi: 10.1111/febs.16371. Epub 2022 Feb 4.

Abstract

The UbiX/UbiD system is widespread in microbes and responsible for the reversible decarboxylation of unsaturated carboxylic acids. The UbiD enzyme catalyzes this unusual reaction using a prenylated flavin (prFMN) as cofactor, the latter formed by the flavin prenyltransferase UbiX. A detailed picture of the biochemistry of flavin prenylation, oxidative maturation, and covalent catalysis underpinning reversible decarboxylation is emerging. This reveals the prFMN cofactor can undergo a wide range of transformations, complemented by considerable UbiD-variability. These provide a blueprint for biotechnological applications aimed at producing hydrocarbons or aromatic C-H activation through carboxylation.

Keywords: (de) carboxylation; UbiD; UbiX; flavin chemistry; prFMN.

Publication types

  • Review
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxy-Lyases* / genetics
  • Carboxy-Lyases* / metabolism
  • Dimethylallyltranstransferase* / chemistry
  • Dimethylallyltranstransferase* / genetics
  • Dimethylallyltranstransferase* / metabolism
  • Flavin Mononucleotide / chemistry
  • Flavins / metabolism
  • Oxidation-Reduction

Substances

  • Flavins
  • Carboxy-Lyases
  • Flavin Mononucleotide
  • Dimethylallyltranstransferase
  • 4,6-dinitro-o-cresol