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

被引：14

作者：

Shi, Wei ^{[1
,2
,3
]}

Tang, Feng ^{[1
,3
]}

Ao, Jiwei ^{[1
]}

Yu, Qun ^{[1
]}

Liu, Junjie ^{[1
]}

Tang, Yubo ^{[1
]}

Jiang, Bofeng ^{[1
]}

Ren, Xuelian ^{[1
]}

Huang, He ^{[1
,2
]}

Yang, Weibo ^{[1
,2
,3
]}

Huang, Wei ^{[1
,2
,3
]}

机构：

[1] 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

[2] Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China

[3] Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 45期

基金：

中国国家自然科学基金;

关键词：

acylation; click chemistry; peptides; rearrangements; silver; COPPER-FREE; CYCLOADDITION; IGG;

D O I：

10.1002/anie.202009408

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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.

引用

页码：19940 / 19944

页数：5

共 2 条

[1] One-Pot, Three-Component Copper-Catalysed 'Click' Triazole Synthesis Utilising the Inexpensive, Shelf-Stable Diazotransfer Reagent Imidazole-1-sulfonyl Azide Hydrochloride
Smith, Neal M.
Greaves, Michelle J.
Jewell, Robert
Perry, Matthew W. D.
Stocks, Michael J.
Stonehouse, Jeffrey P.
SYNLETT, 2009, (09) : 1391 - 1394
[2] Macroporous polymer supported azide and nanocopper (I): efficient and reusable reagent and catalyst for multicomponent click synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides
Keshavarz, Mosadegh
Iravani, Nasir
Ghaedi, Abdolmohammad
Ahmady, Amanollah Zarei
Vafaei-Nezhad, Masoumeh
Karimi, Sara
SPRINGERPLUS, 2013, 2

← 1 →