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

CORC > 兰州化学物理研究所 > 中国科学院兰州化学物理研究所 > OSSO国家重点实验室

	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
	Xu, Kai 1; Wang, Yong 2; Hirao, Hajime 1
刊名	ACS Catalysis
	2015
卷号	5 期号:7 页码:4175-4179
关键词	aromatase Cpd I QM/MM H-abstraction PCET
ISSN号	2155-5435
通讯作者	Wang, Yong ; Hirao, Hajime
英文摘要	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.
学科主题	物理化学与绿色催化
收录类别	SCI
资助信息	the CINECA award N. HP10BO043N, 2010 for the availability of high performance computing resources and support
语种	英语
WOS记录号	WOS:000357626800033
公开日期	2015-12-24
内容类型	期刊论文
源URL	[http://210.77.64.217/handle/362003/18502]
专题	兰州化学物理研究所_OSSO国家重点实验室
作者单位	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
推荐引用方式 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.