Why is firefly oxyluciferin a notoriously labile substance?

Oleg V. Maltsev, Naba K. Nath, Pance Naumov, Lukas Hintermann

Research output: Contribution to journalArticle

Abstract

The chemistry of firefly bioluminescence is important for numerous applications in biochemistry and analytical chemistry. The emitter of this bioluminescent system, firefly oxyluciferin, is difficult to handle. The cause of its lability was clarified while its synthesis was reinvestigated. A side product was identified and characterized by NMR spectroscopy and X-ray crystallography. The reason for the lability of oxyluciferin is now ascribed to autodimerization of the coexisting enol and keto forms in a Mannich-type reaction. Light into the darkness: Firefly oxyluciferin, the emitter of firefly bioluminescence, is notoriously difficult to handle. The cause behind its chemical lability is now ascribed to autodimerization of the coexisting enol (showing blue fluorescence in DMSO) and keto forms (contributing to the green fluorescence in water) in a Mannich reaction.

Original languageEnglish (US)
Pages (from-to)847-850
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number3
DOIs
Publication statusPublished - Jan 14 2014

    Fingerprint

Keywords

  • bioorganic chemistry
  • heterocycles
  • luminescence
  • natural products
  • structure elucidation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this