Horseradish peroxidase (HRP) catalyzed oxidative coupling reactions using aqueous hydrogen peroxide: an environmentally benign procedure for the synthesis of azine pigments

被引：17
作者：
Bodtke, A
Pfeiffer, WD
Ahrens, N
Langer, P
机构：
[1] Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany
[2] Univ Greifswald, Klin Neurol, D-17487 Greifswald, Germany
[3] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[4] Univ Rostock eV, Leibniz Inst Organ Katalyse, D-18059 Rostock, Germany
来源：
TETRAHEDRON | 2005年 / 61卷 / 46期
关键词：
azines; enzymatic reactions; heterocycles; oxidation; peroxidase;
D O I：
10.1016/j.tet.2005.08.103
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The horseradish peroxidase (HRP) catalyzed oxidative coupling of 2-hydrazono-4-thiazolines with a-naphthol using aqueous hdrogen peroxide. These transformations allow an environmentally benign synthesis of p-naphthoquinone-thiazol-2-on-azines under mild conditions. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：10926 / 10929
页数：4
相关论文
共 13 条
[1]   The catalytic pathway of horseradish peroxidase at high resolution [J].
Berglund, GI ;
Carlsson, GH ;
Smith, AT ;
Szöke, H ;
Henriksen, A ;
Hajdu, J .
NATURE, 2002, 417 (6887) :463-468
[2]  
BEYER H, 1969, Z CHEM, V10, P361
[3]   Peroxidase catalyzed formation of azine pigments - a convenient and sensitive method for the identification of human cells with positive myeloperoxidase reactivity [J].
Bodtke, A ;
Pfeiffer, WD ;
Ahrens, N ;
Langer, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (06) :1509-1511
[4]   Laccase-catalyzed carbon-carbon bond formation: oxidative dimerization of salicylic esters by air in aqueous solution [J].
Ciecholewski, S ;
Hammer, E ;
Manda, K ;
Bose, G ;
Nguyen, VTH ;
Langer, P ;
Schauer, F .
TETRAHEDRON, 2005, 61 (19) :4615-4619
[5]  
HUNIG S, 1957, LIEBIGS ANN CHEM, V609, P143
[6]   HETEROCYCLIC AZO DYES BY OXYDATIVE COUPLING [J].
HUNIG, S ;
BALLI, H ;
FRITSCH, KH ;
HERRMANN, H ;
KOBRICH, G ;
WERNER, H ;
GRIGAT, E ;
MULLER, F ;
NOTHER, H ;
OETTE, KH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1958, 70 (08) :215-222
[7]   Lipase-catalyzed highly enantioselective kinetic resolution of racemic α-hydroxy butenolides [J].
Kirschner, A ;
Langer, P ;
Bornscheuer, UT .
TETRAHEDRON-ASYMMETRY, 2004, 15 (18) :2871-2874
[8]   SYNTHESIS OF 4-(DELTA-4-THIAZOLIN-2-YLIDEN-HYDRAZONO)-DELTA-2-PYRAZOLIN-5-ONES BY OXIDATIVE COUPLING [J].
PFEIFFER, WD ;
BULKA, E ;
AHRENS, N .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1992, 334 (04) :365-366
[9]  
PFEIFFER WD, 1997, HOUBENWEYL METHO E C, V9
[10]  
PFEIFFER WD, 1992, Patent No. 4113223
12