37156-84-6Relevant articles and documents
Synthesis of 2-amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine
Kakoi, Hisae
, p. 301 - 302 (2002)
2-Amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine (2), a precursor of Watasenia preluciferin (coelenterazine) (1), is widely distributed in marine bioluminescent animals. It was prepared from p-hydroxyphenylglyoxal aldoxime (5) in two steps; by condensation wi
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.
Multicomponent synthesis of novel coelenterazine derivatives substituted at the C-3 position
Vece, Vito,Vuocolo, Giuseppina
, p. 8781 - 8785 (2015/10/28)
Three novel coelenterazine derivatives substituted at the C-3 position were synthesized through a multicomponent strategy based on Groebke-Blackburn-Bienaymé reaction without using protecting groups. An efficient one-pot tert-butyl group cleavage from an