Synthesis, Characterization, and Reactivity of Hypochloritoiron(III) Porphyrin Complexes

被引：38
|
作者：
Cong, Zhiqi [1 ,2 ]
Yanagisawa, Sachiko [3 ,4 ]
Kurahashi, Takuya [1 ,2 ]
Ogura, Takashi [3 ,4 ]
Nakashima, Satoru [3 ,4 ]
Fujii, Hiroshi [1 ,2 ]
机构：
[1] Natl Inst Nat Sci, Inst Mol Sci, Okazaki, Aichi 4448787, Japan
[2] Natl Inst Nat Sci, Okazaki Inst Integrat Biosci, Okazaki, Aichi 4448787, Japan
[3] Univ Hyogo, Grad Sch Life Sci, Dept Life Sci, Koto Ku, Ako, Hyogo 6781297, Japan
[4] Univ Hyogo, Grad Sch Life Sci, Picobiol Inst, Koto Ku, Ako, Hyogo 6781297, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 51期
关键词：
CHLOROPEROXIDASE COMPOUND-I; NUCLEAR-MAGNETIC-RESONANCE; PI-CATION RADICALS; OXIDATION REACTIONS; OLEFIN EPOXIDATION; HYDROGEN-PEROXIDE; OXYGEN SOURCE; MYELOPEROXIDASE; CHLORIDE; HEME;
D O I：
10.1021/ja3108774
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A hypochloritoiron(III) porphyrin species has been proposed as a key intermediate in an antimicrobial defense system in neutrophils and in hemecatalyzed chlorination reactions. We report herein the preparation, spectroscopic characterization, and reactivity of the bis(hypochlorito)iron(III) porphyrin complex [(TPFP)Fe-III(OC1)(2)](-) (1) and the imidazole-hypochloritoiron complexes (TPFP)Fe-III(OC1)(1-R-Im) [R = CH3 (2), H (3), CH2CO2H (4)], in which TPFP is 5,10,15,20-tetrakis(pentafluorophenyl)porphyrinate. The structures of 1-4 were confirmed by absorption, H-2 and F-19 NMR, EPR, and resonance Raman spectroscopy and electrospray ionization mass spectrometry at low temperature. The reactions of 1 and 2 with various organic substrates show that 1 and 2 are capable of chlorination, sulfoxidation, and epoxidation reactions and that 1 is much more reactive with these substrates than 2.
引用
收藏
页码：20617 / 20620
页数：4
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