Extreme rate acceleration by axial thiolate coordination on the isomerization of endoperoxide catalyzed by iron porphyrin

被引：20

作者：

Yamane, Takehiro ^{[1
]}

Makino, Kohei ^{[1
]}

Umezawa, Naoki ^{[1
]}

Kato, Nobuki ^{[1
]}

Higuchi, Tsunehiko ^{[1
]}

机构：

[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 34期

关键词：

cytochrome P450; endoperoxides; enzyme models; heme; ligand effects;

D O I：

10.1002/anie.200800137

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A coordinated effort: The isomerization mechanism of prostaglandin H2 (PGH2), which is catalytically isomerized to prostacyclin or thromboxane A2 by cytochrome P450s, was investigated using a hemethiolate complex and an endoperoxide. Isomerization of endoperoxides proceeded very rapidly with this complex, whereas imidazole- or chloride-ligated heme had slight or no catalytic activity (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6438 / 6440

页数：3

共 22 条

[1] PROSTANOID ENDOPEROXIDE MODEL COMPOUNDS - 2,3-DIOXABICYCLO[2.2.1]HEPTANE VIA SELECTIVE DIIMIDE REDUCTION [J].

ADAM, W ;

EGGELTE, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) :3987-3988

[2] SYNTHESIS AND THERMAL REACTIVITY OF SOME 2,3-DIOXABICYCLO[2.2.1]HEPTANE MODELS OF PROSTAGLANDIN ENDOPEROXIDES [J].

COUGHLIN, DJ ;

SALOMON, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) :655-657

[3] PROBING STRUCTURE-FUNCTION RELATIONS IN HEME-CONTAINING OXYGENASES AND PEROXIDASES [J].

DAWSON, JH .

SCIENCE, 1988, 240 (4851) :433-439

[4] Structure and chemistry of cytochrome P450 [J].

Denisov, IG ;

Makris, TM ;

Sligar, SG ;

Schlichting, I .

CHEMICAL REVIEWS, 2005, 105 (06) :2253-2277

[5]

DEWITT DL, 1983, J BIOL CHEM, V258, P3285

[6]

EDWARD GJ, 1981, CAN J CHEM, V59, P756

[7]

Groves J.T., 2000, PORPHYRIN HDB, V4, P17

[8]

HARA S, 1994, J BIOL CHEM, V269, P19897

[9]

HECKER M, 1989, J BIOL CHEM, V264, P141

[10] SYNTHESIS OF A HIGHLY STABLE IRON PORPHYRIN COORDINATED BY ALKYLTHIOLATE ANION AS A MODEL FOR CYTOCHROME-P-450 AND ITS CATALYTIC ACTIVITY IN O-O BOND-CLEAVAGE [J].

HIGUCHI, T ;

UZU, S ;

HIROBE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7051-7053

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