Synthesis of cytochrome c oxidase models bearing a Tyr244 mimic

被引:33
作者
Collman, JP [1 ]
Decréau, RA [1 ]
Zhang, C [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/jo0499625
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A close structural analogue of the metal-free cytochrome c oxidase active site has been synthesized. This model has a proximal imidazole tail and three distal imidazole pickets attached to a porphyrin. One distal imidazole is cross-linked to a phenol, mimicking Tyr(244). The strategy behind the successful synthesis of this regioisomerically pure model involved discovering the best sequence to introduce the phenol-substituted imidazole and employing a fluorinated substituent.
引用
收藏
页码:3546 / 3549
页数:4
相关论文
共 24 条
[1]   UV resonance Raman characterization of model compounds of Tyr244 of bovine cytochrome c oxidase in its neutral, deprotonated anionic, and deprotonated neutral radical forms:: Effects of covalent binding between tyrosine and histidine [J].
Aki, M ;
Ogura, T ;
Naruta, Y ;
Le, TH ;
Sato, T ;
Kitagawa, T .
JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (14) :3436-3444
[2]   Functional analogues of the dioxygen reduction site in cytochrome oxidase:: Mechanistic aspects and possible effects of CuB [J].
Boulatov, R ;
Collman, JP ;
Shiryaeva, IM ;
Sunderland, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11923-11935
[3]   Modeling the active site of cytochrorne oxidase:: Synthesis and characterization of a cross-linked histidine-phenol [J].
Cappuccio, JA ;
Ayala, I ;
Elliott, GI ;
Szundi, I ;
Lewis, J ;
Konopelski, JP ;
Barry, BA ;
Einarsdóttir, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1750-1760
[4]   Efficient synthesis of 1-substituted-5-hydroxymethylimidazole derivatives: Clean oxidative cleavage of 2-mercapto group [J].
Chang, JH ;
Lee, KW ;
Nam, DH ;
Kim, WS ;
Shin, K .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (05) :674-676
[5]   Water-soluble polymer-bound biomimetic analogues of cytochrome c oxidase catalyze 4e- reduction of O2 to water [J].
Collman, JP ;
Fudickar, W ;
Shiryaeva, I .
INORGANIC CHEMISTRY, 2003, 42 (11) :3384-3386
[6]   Biomimetic studies of terminal oxidases: Trisimidazole picket metalloporphyrins [J].
Collman, JP ;
Sunderland, CJ ;
Boulatov, R .
INORGANIC CHEMISTRY, 2002, 41 (08) :2282-2291
[7]  
Collman JP, 2002, ANGEW CHEM INT EDIT, V41, P3487, DOI 10.1002/1521-3773(20020916)41:18<3487::AID-ANIE3487>3.0.CO
[8]  
2-Y
[9]   New imidazole-based tripodal ligands as CuB site mimics of cytochrome c oxidase [J].
Collman, JP ;
Zhong, M ;
Costanzo, S ;
Zhang, C .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8252-8256
[10]   Novel protecting strategy for the synthesis of porphyrins with different distal and proximal superstructures [J].
Collman, JP ;
Bröring, M ;
Fu, L ;
Rapta, M ;
Schwenninger, R ;
Straumanis, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8082-8083