coelenterazine
Sign in to saveAlso known as Oplophorus luciferin, coelenterate luciferin, 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo-[1,2a]pyrazin-3(7H)-one
Coelenterazine is a luciferin, a molecule that emits light after reaction with oxygen, found in many aquatic organisms across eight phyla. It is the substrate of many luciferases such as Renilla reniformis luciferase (Rluc), Gaussia luciferase (Gluc), and photoproteins, including aequorin, and obelin. All these proteins catalyze the oxidation of this substance, a reaction catalogued EC 1.13.12.5.
Research
574 papersvia PubMed
Wikidata facts
- Mass
- 423.158
Show 3 more facts
- canonical SMILES
- OC=1C=CC(=CC1)C=2N=C(C3=NC(=C(O)N3C2)CC4=CC=C(O)C=C4)CC=5C=CC=CC5
- chemical formula
- C₂₆H₂₁N₃O₃
- Commons category
- Coelenterazine
Sources (2)
via Wikidata · CC0
~3 min read
Article
10 sectionsContents
- History
- Occurrence
- Biosynthesis
- Properties
- Bioluminescence
- Synthetic coelenterazine derivatives
- See also
- References
- External links
- External links
Coelenterazine is a luciferin, a molecule that emits light after reaction with oxygen, found in many aquatic organisms across eight phyla. It is the substrate of many luciferases such as Renilla reniformis luciferase (Rluc), Gaussia luciferase (Gluc), and photoproteins, including aequorin, and obelin. All these proteins catalyze the oxidation of this substance, a reaction catalogued EC 1.13.12.5.
==History== Coelenterazine was simultaneously isolated and characterized by two groups studying the luminescent organisms sea pansy (Renilla reniformis) and the cnidarian Aequorea victoria, respectively. Both groups independently discovered that the same compound was used in both luminescent systems. The molecule was named after the now-obsolete phylum coelenterata. Likewise, the two main metabolites – coelenteramide and coelenteramine – were named after their respective functional groups. While coelenterazine was first discovered in Aequorea victoria, it was later shown that they do not synthesize coelenterazine, but obtain it through their diet, largely from crustaceans and copepods.