Metalloporphyrin and heteropoly acid catalyzed oxidation of C=NOH bonds in an ionic liquid: biomimetic models of nitric oxide synthase

被引:73
作者
Jain, N [1 ]
Kumar, A [1 ]
Chauhan, SMS [1 ]
机构
[1] Univ Delhi, Dept Chem, Delhi 110007, India
关键词
nitric oxide synthase (NOS); heteropoly acid; porphyrins; ionic liquid;
D O I
10.1016/j.tetlet.2005.02.088
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Water soluble iron(III) porphyrins and phosphotungstic acid in an ionic liquid are effective catalysts for the H2O2 mediated oxidation of the C=NOH bond in N-hydroxyarginine and other oximes. The carbonyl compounds generated as the oxidation products can be easily isolated from the reaction media. These systems serve as biomimetic models of nitric oxide synthase (NOS) and the catalyst immobilized in an ionic liquid can be easily recycled and reused. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2599 / 2602
页数:4
相关论文
共 30 条
[1]  
Akhtar M, 1997, J STEROID BIOCHEM, V61, P127
[2]  
[Anonymous], REV HETEROATOM CHEM
[3]   Reaction of neuronal nitric-oxide synthase with oxygen at low temperature - Evidence for reductive activation of the oxy-ferrous complex by tetrahydrobiopterin [J].
Bec, N ;
Gorren, ACF ;
Voelker, C ;
Mayer, B ;
Lange, R .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (22) :13502-13508
[4]   Biomimetic oxidation of curcumin with hydrogen peroxide catalyzed by 5,10,15,20-tetraarylporphyrinato-iron(III) chlorides in dichloromethane [J].
Chauhan, SMS ;
Kandadai, AS ;
Jain, N ;
Kumar, A .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (11) :1345-1347
[5]   Oxidation of thiols with molecular oxygen catalyzed by cobalt(II) phthalocyanines in ionic liquid [J].
Chauhan, SMS ;
Kumar, A ;
Srinivas, KA .
CHEMICAL COMMUNICATIONS, 2003, (18) :2348-2349
[6]   Biomimetic oxidation of ibuprofen with hydrogen peroxide catalysed by horseradish peroxidase (HRP) and 5,10,15,20-tetrakis-(2′,6′-dichloro-3′-sulphonatophenyl) and manganese(III) hydrates in AOT reverse micelles [J].
Chauhan, SMS ;
Sahoo, BB .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (11) :2629-2634
[7]   INORGANIC SOLID ACIDS AND THEIR USE IN ACID-CATALYZED HYDROCARBON REACTIONS [J].
CORMA, A .
CHEMICAL REVIEWS, 1995, 95 (03) :559-614
[8]   Ionic liquid (molten salt) phase organometallic catalysis [J].
Dupont, J ;
de Souza, RF ;
Suarez, PAZ .
CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691
[9]  
HEVEL JM, 1993, ADV EXP MED BIOL, V338, P285
[10]   HOMOGENEOUS CATALYSIS BY TRANSITION-METAL OXYGEN ANION CLUSTERS [J].
HILL, CL ;
PROSSERMCCARTHA, CM .
COORDINATION CHEMISTRY REVIEWS, 1995, 143 :407-455