Manipulating the Click Reactivity of Dibenzoazacyclooctynes: From Azide Click Component to Caged Acylation Reagent by Silver Catalysis

doi:10.1002/anie.202009408

	Manipulating the Click Reactivity of Dibenzoazacyclooctynes: From Azide Click Component to Caged Acylation Reagent by Silver Catalysis
	Shi, Wei 1,2,3; Tang, Feng 1,2; Ao, Jiwei 2; Yu, Qun 2; Liu, Junjie 2; Tang, Yubo 2; Jiang, Bofeng 2; Ren, Xuelian 2; Huang, He 2,3; Yang, Weibo 1,2,3
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2020-08-31
页码	6
关键词	acylation click chemistry peptides rearrangements silver
ISSN号	1433-7851
DOI	10.1002/anie.202009408
通讯作者	Yang, Weibo(yweibo@simm.ac.cn) ; Huang, Wei(huangwei@simm.ac.cn)
英文摘要	Strain-promoted azide-alkyne cycloaddition using dibenzoazacyclooctyne (DBCO) is widely applied in copper-free bioorthogonal reactions. Reported here is the efficient acid-promoted rearrangement and silver-catalyzed amidation of DBCO, which alters its click reactivity robustly. In the switched click reaction, DBCO, as a caged acylation reagent, enables rapid peptide/protein modification after decaging facilitated by silver catalysts, rendering site-specific conjugation of an IgG antibody by a Fc-targeting peptide.
资助项目	National Natural Science Foundation of China (NNSFC)[21877116] ; National Natural Science Foundation of China (NNSFC)[21702217] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program of China[2018ZX09711002-006] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program of China[2019ZX09721001] ; Shanghai-Technology Innovation Action Plan[18JC1415300]
WOS关键词	COPPER-FREE ; CYCLOADDITION ; IGG
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000567290000001
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/291119]
专题	中国科学院上海药物研究所
通讯作者	Yang, Weibo; Huang, Wei
作者单位	1.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China 2.Chinese Acad Sci, CAS Ctr Excellence Mol Cell Sci, Ctr Biotherapeut Discovery Res, Shanghai Inst Mat Med,CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China 3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Shi, Wei,Tang, Feng,Ao, Jiwei,et al. Manipulating the Click Reactivity of Dibenzoazacyclooctynes: From Azide Click Component to Caged Acylation Reagent by Silver Catalysis[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020:6.
APA	Shi, Wei.,Tang, Feng.,Ao, Jiwei.,Yu, Qun.,Liu, Junjie.,...&Huang, Wei.(2020).Manipulating the Click Reactivity of Dibenzoazacyclooctynes: From Azide Click Component to Caged Acylation Reagent by Silver Catalysis.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,6.
MLA	Shi, Wei,et al."Manipulating the Click Reactivity of Dibenzoazacyclooctynes: From Azide Click Component to Caged Acylation Reagent by Silver Catalysis".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020):6.