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Theoretical study of the mechanism of acetaldehyde hydroxylation by compound I of CYP2E1
Wang, Y; Wang, HM; Wang, YH; Yang, CL; Yang, L; Han, KL
Source PublicationJOURNAL OF PHYSICAL CHEMISTRY B
2006-03-30
DOI10.1021/jp060033m
Volume110Issue:12Pages:6154-6159
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Physical
WOS Research AreaChemistry
WOS KeywordC-H HYDROXYLATION ; 2-STATE REBOUND MECHANISM ; GAUSSIAN-BASIS SETS ; ELECTRONIC-STRUCTURE ; CYTOCHROME-P450 ENZYMES ; REACTIVITY PATTERNS ; AXIAL LIGAND ; ROW ATOMS ; OXIDATION ; MODEL
AbstractRecent 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.
Language英语
WOS IDWOS:000236407400046
Citation statistics
Cited Times:24[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/140209
Collection中国科学院大连化学物理研究所
Affiliation1.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
GB/T 7714
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.
APA Wang, Y,Wang, HM,Wang, YH,Yang, CL,Yang, L,&Han, KL.(2006).Theoretical study of the mechanism of acetaldehyde hydroxylation by compound I of CYP2E1.JOURNAL OF PHYSICAL CHEMISTRY B,110(12),6154-6159.
MLA Wang, Y,et al."Theoretical study of the mechanism of acetaldehyde hydroxylation by compound I of CYP2E1".JOURNAL OF PHYSICAL CHEMISTRY B 110.12(2006):6154-6159.
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