Chemistry:Coelenteramide
Coelenteramide is the oxidized product, or oxyluciferin, of the bioluminescent reactions in many marine organisms that use coelenterazine. It was first isolated as a blue fluorescent protein from Aequorea victoria after the animals were stimulated to emit light.[1] Under basic conditions, the compound will break down further into coelenteramine and 4-hydroxyphenylacetic acid.
It is an aminopyrazine.[2]
Biosynthesis
Biosynthesis of the precursor coelenterazine in Mnemiopsis leidyi and related comb jellies starts from two molecules of tyrosine and one molecule of phenylalanine. Some researchers believe this comes in the form of a cyclized "Phe-Tyr-Tyr" (FYY) peptide,[3] but as of 2025[update] the full details of the pathway were not known.[4][5]
Bioluminescence
Enzymes such as renilla-luciferin 2-monooxygenase are responsible for the bioluminescence observed in the organisms which contain coelenterazine by catalyzing the chemical reaction
In the process, coelenterazine is oxidized with a concurrent loss of carbon dioxide, and a photon of blue light is emitted.[6]
References
- ↑ Shimomura O, Johnson FH (1975). "Chemical Nature of Bioluminescence Systems in Coelenterates". PNAS USA 72 (4): 1546–1549. doi:10.1073/pnas.72.4.1546. PMID 236561. Bibcode: 1975PNAS...72.1546S.
- ↑ Discovery and Validation of a New Family of Antioxidants: The Aminopyrazine Derivatives. M. L. N. Dubuisson, J.-F. Rees and J. Marchand-Brynaert, Mini-Reviews in Medicinal Chemistry, 2004, 4, 159-165, doi:10.2174/1389557043403927
- ↑ Francis, Warren R.; Shaner, Nathan C.; Christianson, Lynne M.; Powers, Meghan L.; Haddock, Steven H. D. (2015). "Occurrence of Isopenicillin-N-Synthase Homologs in Bioluminescent Ctenophores and Implications for Coelenterazine Biosynthesis". PLOS ONE 10 (6). doi:10.1371/journal.pone.0128742. PMID 26125183.
- ↑ Tsarkova, Aleksandra S. (2021). "Luciferins Under Construction: A Review of Known Biosynthetic Pathways". Frontiers in Ecology and Evolution 9. doi:10.3389/fevo.2021.667829.
- ↑ Oba, Yuichi (2025). "Copepod luminescence revisited". Plankton and Benthos Research 20: s1–s11. doi:10.3800/pbr.20.s1.
- ↑ Loening, Andreas Markus; Fenn, Timothy David; Gambhir, Sanjiv Sam (2007). "Crystal Structures of the Luciferase and Green Fluorescent Protein from Renilla reniformis". Journal of Molecular Biology 374 (4): 1017–1028. doi:10.1016/j.jmb.2007.09.078. PMID 17980388.
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