50611-86-4Relevant academic research and scientific papers
Formation of Coelenteramine from 2-Peroxycoelenterazine in the Ca2+-Binding Photoprotein Aequorin
Hosoya, Takamitsu,Inouye, Satoshi,Nakamura, Mitsuhiro
, (2022/01/19)
Aequorin consists of apoprotein (apoAequorin) and (S)-2-peroxycoelenterazine (CTZ-OOH) and is considered to be a transient-state complex of an enzyme (apoAequorin) and a substrate (coelenterazine and molecular oxygen) in the enzymatic reaction. The degradation process of CTZ-OOH in aequorin was characterized under various conditions of protein denaturation. By acid treatment, the major product from CTZ-OOH was coelenteramine (CTM), but not coelenteramide (CTMD), and no significant luminescence was observed. The counterparts of CTM from CTZ-OOH were identified as 4-hydroxyphenylpyruvic acid (4HPPA) and 4-hydroxyphenylacetic acid (4HPAA) by liquid chromatography/electrospray ionization–time-of-flight mass spectrometry (LC/ESI-TOF-MS). In the luminescence reaction of aequorin with Ca2+, similar amounts of 4HPPA and 4HPAA were detected, indicating that CTM is formed by two pathways from CTZ-OOH through dioxetanone anion and not by hydrolysis from CTMD.
Process for producing coelenteramide or an analog thereof
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Page/Page column 46-47, (2011/10/12)
A process for producing coelenteramide or its analog in a high yield has been desired. The invention provides a process for producing di-O-methylcoelenteramide or its analog of formula (3) which comprises reacting O-methylcoelenteramine or its analog with
Synthesis, structural characterization and antioxidative properties of aminopyrazine and imidazolopyrazine derivatives
Devillers, Ingrid,De Wergifosse, Bertrand,Bruneau, Marie-Pierre,Tinant, Bernard,Declercq, Jean-Paul,Touillaux, Roland,Rees, Jean-Francois,Marchand-Brynaert, Jacqueline
, p. 1481 - 1487 (2007/10/03)
The reaction of 2-aminopyrazine 1 with the glyoxal derivatives 2a-c gave the bicyclic imidazolopyrazinones 3a,b and the monocyclic N-substituted aminopyrazines 4b and 5c. Compounds 3 feature unique crystallographic characteristics. Their reactivity towards superoxide anion is about five times the reactivity of Trolox , while the monocyclic pyrazines are inactive.
Chemi- and Bio-luminescence of Coelenterazine Analogues with Phenyl Homologues at the C-2 Position
Qi, Chen Feng,Gomi, Yasushiro,Hirano, Takashi,Ohashi, Mamoru,Ohmiya, Yoshihiro,Tsuji, Frederick I.
, p. 1607 - 1612 (2007/10/02)
A series of phenyl homologues of coelenterazine substituted at the C-2 position were synthesized and their bio- and chemi-luminescence properties were investigated including the measurement of chemiluminescence spectra in various media.The light emitting species of each analogue was found to be a neutral form of a coelenteramide derivative in diethylene glycol dimethyl ether (DGM) containing a trace amount of acetate buffer (pH 5.60), while a monoanion was found only in dimethyl sulfoxide (DMSO) and a dianion was observed in DMSO containing a trace amount of aqueous sodium hydroxide.Based on pseudo first-order reaction kinetics, chemiluminescence rate constants were obtained in DGM containing a trace amount of acetate buffer.Each of the synthetic coelenterazine analogues was incorporated into recombinant apoaequorin to obtain a series of semisynthetic aequorins.Measurements of bioluminescence activities of the aequorins revealed that a benzyl group in the C-2 position was essential for efficient luminescence activity.A two-step incubation procedure was used to determine why some analogues gave less luminescence activity than the benzyl analogue and natural coelenterazine.
