Investigating the Proteome Reactivity and Selectivity of Aryl Halides

doi:10.1021/ja4116204

CORC > 北京大学 > 化学与分子工程学院

	Investigating the Proteome Reactivity and Selectivity of Aryl Halides
	Shannon, D. Alexander ; Banerjee, Ranjan ; Webster, Elizabeth R. ; Bak, Daniel W. ; Wang, Chu ; Weerapana, Eranthie
刊名	journal of the american chemical society
	2014
关键词	ACTIVITY-BASED PROBES CHEMICAL PROTEOMICS ELECTROPHILES CHEMISTRY PROTEASES MECHANISM COVALENT SITES
DOI	10.1021/ja4116204
英文摘要	Protein-reactive electrophiles are critical to chemical proteomic applications including activity-based protein profiling, site-selective protein modification, and covalent inhibitor development. Here, we explore the protein reactivity of a panel of aryl halides that function through a nucleophilic aromatic substitution (SNAr) mechanism. We show that the reactivity of these electrophiles can be finely tuned by varying the substituents on the aryl ring. We identify p-chloro- and fluoronitrobenzenes and dichlorotriazines as covalent protein modifiers at low micromolar concentrations. Interestingly, investigating the site of labeling of these electrophiles within complex proteomes identified p-chloronitrobenzene as highly cysteine selective, whereas the dichlorotriazine favored reactivity with lysines. These studies illustrate the diverse reactivity and amino-acid selectivity of aryl halides and enable the future application of this class of electrophiles in chemical proteomics.; Chemistry, Multidisciplinary; SCI(E); EI; 4; ARTICLE; eranthie@bc.edu; 9; 3330-3333; 136
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/389691]
专题	化学与分子工程学院生命科学学院
推荐引用方式 GB/T 7714	Shannon, D. Alexander,Banerjee, Ranjan,Webster, Elizabeth R.,et al. Investigating the Proteome Reactivity and Selectivity of Aryl Halides[J]. journal of the american chemical society,2014.
APA	Shannon, D. Alexander,Banerjee, Ranjan,Webster, Elizabeth R.,Bak, Daniel W.,Wang, Chu,&Weerapana, Eranthie.(2014).Investigating the Proteome Reactivity and Selectivity of Aryl Halides.journal of the american chemical society.
MLA	Shannon, D. Alexander,et al."Investigating the Proteome Reactivity and Selectivity of Aryl Halides".journal of the american chemical society (2014).