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Why is Firefly Oxyluciferin a Notoriously Labile Substance?
Author(s) -
Maltsev Oleg V.,
Nath Naba K.,
Naumov Panče,
Hintermann Lukas
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201307972
Subject(s) - lability , firefly protocol , bioluminescence , chemistry , nuclear magnetic resonance spectroscopy , diacetylene , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , biology , polymerization , polymer , zoology
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.