Studies on the mechanism of chemiluminescence: Synthesis and chemiluminescent properties of the 5-hydroperoxide analogue of coelenterate luciferin

被引:8
作者
Teranishi, K
Hisamatsu, M
Yamada, T
机构
[1] Faculty of Bioresources, Mie University, Kamihama, Tsu
关键词
D O I
10.1016/0040-4039(96)01927-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 5-hydroperoxide analogue of coelenterate luciferin has been synthesized and is one of the postulated intermediates in chemiluminescent reactions of coelenterate luciferin, Cypridina luciferin, and its analogues. The 5-hydroperoxide analogue emitted weak light in chemiluminescent reactions in several solvent systems. However, it did pot generate any amide. This research leads to the conclusion that 5-hydroperoxide is not an important intermediate in chemiluminescent reactions. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:8425 / 8428
页数:4
相关论文
共 28 条
[1]   CHEMILUMINESCENCE OF CIPRIDINA LUCIFERIN ANALOGS .2. KINETIC-STUDIES ON THE REACTION OF 2-METHYL-6-PHENYLIMIDAZO[1,2-A]PYRAZIN-3(7H)-ONE (CLA) WITH SUPEROXIDE - HYDROPEROXYL RADICAL IS AN ACTUAL ACTIVE SPECIES USED TO INITIATE THE REACTION [J].
AKUTSU, K ;
NAKAJIMA, H ;
KATOH, T ;
KINO, S ;
FUJIMORI, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (08) :1699-1706
[2]   CHEMILUMINESCENCE OF CYPRIDINA LUCIFERIN ANALOGS .1. EFFECT OF PH ON RATES OF SPONTANEOUS AUTOXIDATION OF CLA IN AQUEOUS BUFFER SOLUTIONS [J].
FUJIMORI, K ;
NAKAJIMA, H ;
AKUTSU, K ;
MITANI, M ;
SAWADA, H ;
NAKAYAMA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (12) :2405-2409
[3]   CYPRIDINA BIOLUMINESCENCE .10. CHEMI-LUMINESCENCE OF A CYPRIDINA LUCIFERIN ANALOG, 2-METHYL-6-PHENYL-3,7-DIHYDROIMIDAZO[1,2-A]PYRAZIN-3-ONE, IN THE PRESENCE OF THE XANTHINE-XANTHINE OXIDASE SYSTEM [J].
GOTO, T ;
TAKAGI, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (03) :833-834
[4]  
GOTO T, 1968, Pure and Applied Chemistry, V17, P421, DOI 10.1351/pac196817030421
[5]  
GOTO T, 1968, TETRAHEDRON LETT, P4035
[6]  
GOTO T, 1968, TETRAHEDRON LETT, P3873
[7]  
GOTO T, 1969, TETRAHEDRON LETT, P4299
[8]  
Haneda Y., 1966, BIOLUMINESCENCE PROG, P67
[9]   CHEMILUMINESCENCE OF COELENTERAZINE ANALOGS - STRUCTURES OF EMITTING SPECIES [J].
HIRANO, T ;
GOMI, Y ;
TAKAHASHI, T ;
KITAHARA, K ;
QI, CF ;
MIZOGUCHI, I ;
KYUSHIN, S ;
OHASHI, M .
TETRAHEDRON LETTERS, 1992, 33 (39) :5771-5774
[10]   MASS-SPECTROMETRIC STUDIES ON CHEMILUMINESCENCE OF COELENTERATE LUCIFERIN ANALOGS [J].
HIRANO, T ;
NISHIBUCHI, S ;
YONEDA, M ;
TSUJIMOTO, K ;
OHASHI, M .
TETRAHEDRON, 1993, 49 (41) :9267-9276