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题名: Theoretical study of the mechanism of acetaldehyde hydroxylation by compound I of CYP2E1
作者: Wang, Y;  Wang, HM;  Wang, YH;  Yang, CL;  Yang, L;  Han, KL
刊名: JOURNAL OF PHYSICAL CHEMISTRY B
发表日期: 2006-03-30
DOI: 10.1021/jp060033m
卷: 110, 期:12, 页:6154-6159
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Physical
研究领域[WOS]: Chemistry
英文摘要: Recent experimental studies revealed that cytochrome P450 2E1 (CYP2E1) could metabolize not only ethanol but also its primary product, acetaldehyde, accompanying the well-known acetaldehyde dehydrogenases (ALDH) in the metabolism of acetaldehyde. Mechanistic aspects of acetaldehyde hydroxylation by Compound I model active species of CYP2E1 were investigated by means of B3LYP DFF calculations in the present paper. Our study results demonstrate that acetaldehyde hydroxylation by CYP2E1 is in accord with the effectively concerted mechanisms both on the high quartet spin state (HS) and on the low doublet spin state (LS). The rate-limiting step is H-abstraction, and the activation energy is about 11.7 similar to 14.0 kcal/mol on the quartet (doublet) reaction route, which is about one-half to one-third of that needed by methane hydroxylation. The phenomenon that the HS and LS reaction routes are both effectively concerted was shown for the first time to occur in trans-2-phenyl-iso-propylcyclopropane hydroxylation by Kumar et al. (see Figure 7 in the paper of Kumar, D.; de Visser, S. P.; Sharma, P. K.; Cohen, S.: Shaik, S. J. Ant. Chem. Soc. 2004, 126, 1907) and was confirmed in our work of acetaldehyde hydroxylation by cytochrome P450. Theoretical exploration of the HS O-rebound barrier degradation is also presented in the present paper on the basis of Shaik's valence bond (VB) model.
关键词[WOS]: C-H HYDROXYLATION ;  2-STATE REBOUND MECHANISM ;  GAUSSIAN-BASIS SETS ;  ELECTRONIC-STRUCTURE ;  CYTOCHROME-P450 ENZYMES ;  REACTIVITY PATTERNS ;  AXIAL LIGAND ;  ROW ATOMS ;  OXIDATION ;  MODEL
语种: 英语
WOS记录号: WOS:000236407400046
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/140209
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
2.Yantai Normal Univ, Dept Phys, Yantai 264025, Peoples R China
3.Chinese Acad Sci, Dalian Inst Chem Phys, Biotechnol Lab, Dalian 116023, Peoples R China

Recommended Citation:
Wang, Y,Wang, HM,Wang, YH,et al. Theoretical study of the mechanism of acetaldehyde hydroxylation by compound I of CYP2E1[J]. JOURNAL OF PHYSICAL CHEMISTRY B,2006,110(12):6154-6159.
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