Novel mechanism of bioluminescence: oxidative decarboxylation of a moiety adjacent to the light emitter of Fridericia luciferin

Angew Chem Int Ed Engl. 2015 Jun 8;54(24):7065-7. doi: 10.1002/anie.201501668. Epub 2015 Apr 27.

Abstract

A novel luciferin from a bioluminescent Siberian earthworm Fridericia heliota was recently described. In this study, the Fridericia oxyluciferin was isolated and its structure elucidated. The results provide insight into a novel bioluminescence mechanism in nature. Oxidative decarboxylation of a lysine fragment of the luciferin supplies energy for light generation, while a fluorescent CompX moiety remains intact and serves as the light emitter.

Keywords: bioluminescence; bioorganic chemistry; luciferin; oxidative decarboxylation; peptides.

Publication types

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

MeSH terms

  • Animals
  • Decarboxylation
  • Indoles / chemistry
  • Luminescent Agents / chemistry*
  • Luminescent Measurements
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Oligochaeta / metabolism*
  • Oxidation-Reduction
  • Pyrazines / chemistry

Substances

  • Indoles
  • Luminescent Agents
  • Pyrazines
  • oxyluciferin