Enzymes
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Reaction participants Show >> << Hide
- Name help_outline O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline Watasenia luciferin Identifier CHEBI:58229 Charge -2 Formula C26H19N3O9S2 InChIKeyhelp_outline PTGHKNQEZNRQKY-UHFFFAOYSA-L SMILEShelp_outline [O-]S(=O)(=O)Oc1ccc(Cc2nc3c(Cc4ccccc4)[nH]c(cn3c2=O)-c2ccc(OS([O-])(=O)=O)cc2)cc1 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CO2 Identifier CHEBI:16526 (Beilstein: 1900390; CAS: 124-38-9) help_outline Charge 0 Formula CO2 InChIKeyhelp_outline CURLTUGMZLYLDI-UHFFFAOYSA-N SMILEShelp_outline O=C=O 2D coordinates Mol file for the small molecule Search links Involved in 980 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline hν Identifier CHEBI:30212 Charge 0 Formula SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 25 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline oxidized Watasenia luciferin Identifier CHEBI:57935 Charge -2 Formula C25H19N3O9S2 InChIKeyhelp_outline OIGFBCOUXJVZJQ-UHFFFAOYSA-L SMILEShelp_outline [O-]S(=O)(=O)Oc1ccc(CC(=O)Nc2ncc(nc2Cc2ccccc2)-c2ccc(OS([O-])(=O)=O)cc2)cc1 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:18057 | RHEA:18058 | RHEA:18059 | RHEA:18060 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Bioluminescence reaction catalyzed by membrane-bound luciferase in the "firefly squid," Watasenia scintillans.
Tsuji F.I.
The small Japanese "firefly squid," Watasenia scintillans, emits a bluish luminescence from dermal photogenic organs distributed along the ventral aspects of the head, mantle, funnel, arms and eyes. The brightest light is emitted by a cluster of three tiny organs located at the tip of each of the ... >> More
The small Japanese "firefly squid," Watasenia scintillans, emits a bluish luminescence from dermal photogenic organs distributed along the ventral aspects of the head, mantle, funnel, arms and eyes. The brightest light is emitted by a cluster of three tiny organs located at the tip of each of the fourth pair of arms. Studies of extracts of the arm organs show that the light is due to a luciferin-luciferase reaction in which the luciferase is membrane-bound. The other components of the reaction are coelenterazine disulfate (luciferin), ATP, Mg(2+), and molecular oxygen. Based on the results, a reaction scheme is proposed which involves a rapid base/luciferase-catalyzed enolization of the keto group of the C-3 carbon of luciferin, followed by an adenylation of the enol group by ATP. The AMP serves as a recognition moiety for docking the substrate molecule to a luciferase bound to membrane, after which AMP is cleaved and a four-membered dioxetanone intermediate is formed by the addition of molecular oxygen. The intermediate then spontaneously decomposes to yield CO(2) and coelenteramide disulfate (oxyluciferin) in the excited state, which serves as the light emitter in the reaction. << Less
Biochim Biophys Acta 1564:189-197(2002) [PubMed] [EuropePMC]
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Bioluminescence of Firefly Squid via Mechanism of Single Electron-Transfer Oxygenation and Charge-Transfer-Induced Luminescence.
Ding B.W., Liu Y.J.
Watasenia scintillans (W. scintillans) is a deep-sea luminescent squid with a popular name of firefly squid. It produces flashes of blue light via a series of complicated luciferin-luciferase reactions involving ATP, Mg<sup>2+</sup>, and molecular oxygen. Tsuji has proposed a hypothetical scheme f ... >> More
Watasenia scintillans (W. scintillans) is a deep-sea luminescent squid with a popular name of firefly squid. It produces flashes of blue light via a series of complicated luciferin-luciferase reactions involving ATP, Mg<sup>2+</sup>, and molecular oxygen. Tsuji has proposed a hypothetical scheme for this mysterious bioluminescence (BL) process, but the proposal is short of strong evidence experimentally or theoretically, especially for two key steps. They are the addition of molecular oxygen to luciferin and the formation of light emitter. For the first time, the present study investigates the two steps by reliable density functional theory (DFT) and time-dependent DFT. The results of calculated energetics, charge transfer process, electronic structures, and molecular dynamics give convincing support for Tsuji's proposal. The oxygenation reaction occurs with a single electron-transfer (SET) mechanism, and the light emitter is produced via the mechanism of gradually reversible charge-transfer-induced luminescence (GRCTIL). The simulation of nonadiabatic molecular dynamics further confirms the GRCTIL mechanisms and evaluates the quantum yield of the light emitter to be 43%. The knowledge obtained in the current study will help to understand a large amount of BL systems in nature, since the core structure of W. scintillans luciferin, imidazopyrazinone, is common in the luciferins of about eight phyla of luminescent organisms. << Less
Comments
Published in: Inoue, S., Kakoi, H. and Goto, T. Squid bioluminescence. III. Isolation and structure of Watasenia luciferin. Tetrahedron Lett., (1976) 2971-2974.