| Estrogen Formation via H-Abstraction from the O-H Bond of gem-Diol by Compound I in the Reaction of CYP19A1: Mechanistic Scenario Derived from Multiscale QM/MM Calculations | |
| Department | OSSO国家重点实验室 |
| Xu, Kai1; Wang, Yong2; Hirao, Hajime1 | |
| 2015 | |
| Source Publication | ACS Catalysis
 |
| ISSN | 2155-5435 |
| Volume | 5Issue:7Pages:4175-4179 |
| Abstract | Recent experiments suggested that, contrary to traditional belief, the third step of aromatase-catalyzed estrogen formation should be effected by compound I (Cpd I), rather than by ferric peroxide. We performed QM/MM calculations to address the question of how Cpd I drives the aromatization process. Surprisingly, the calculations show that the reaction begins with hydrogen abstraction from the O–H bond of a gem-diol substrate, which is followed by barrierless homolytic C–C bond cleavage and then 1β-H-abstraction. Proton-coupled electron transfer enables the cleavage of the strong O–H bond. Another product, carboxylic acid, can be formed from either the gem-diol or aldehyde. |
| Keyword | Aromatase Cpd i Qm/mm H-abstraction Pcet |
| Subject Area | 物理化学与绿色催化 |
| DOI | 10.1021/acscatal.5b00510 |
| Funding Organization | the CINECA award N. HP10BO043N, 2010 for the availability of high performance computing resources and support |
| Indexed By | SCI |
| If | 9.312 |
| Language | 英语 |
| compositor | 第二作者单位 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/18502 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） |
| Corresponding Author | Wang, Yong; Hirao, Hajime |
| Affiliation | 1.Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore 2.Chinese Acad Sci, LICP, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China |
| Recommended Citation GB/T 7714 | Xu, Kai,Wang, Yong,Hirao, Hajime. Estrogen Formation via H-Abstraction from the O-H Bond of gem-Diol by Compound I in the Reaction of CYP19A1: Mechanistic Scenario Derived from Multiscale QM/MM Calculations[J]. ACS Catalysis,2015,5(7):4175-4179. |
| APA | Xu, Kai,Wang, Yong,&Hirao, Hajime.(2015).Estrogen Formation via H-Abstraction from the O-H Bond of gem-Diol by Compound I in the Reaction of CYP19A1: Mechanistic Scenario Derived from Multiscale QM/MM Calculations.ACS Catalysis,5(7),4175-4179. |
| MLA | Xu, Kai,et al."Estrogen Formation via H-Abstraction from the O-H Bond of gem-Diol by Compound I in the Reaction of CYP19A1: Mechanistic Scenario Derived from Multiscale QM/MM Calculations".ACS Catalysis 5.7(2015):4175-4179. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| acs.jcim.5b00249.pdf（4122KB） | 期刊论文 | 出版稿 | 开放获取 | CC BY-NC-SA | View Application Full Text | |
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