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Manipulating the Click Reactivity of Dibenzoazacyclooctynes: From Azide Click Component to Caged Acylation Reagent by Silver Catalysis
Author(s) -
Shi Wei,
Tang Feng,
Ao Jiwei,
Yu Qun,
Liu Junjie,
Tang Yubo,
Jiang Bofeng,
Ren Xuelian,
Huang He,
Yang Weibo,
Huang Wei
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009408
Subject(s) - click chemistry , bioorthogonal chemistry , chemistry , azide , reagent , cycloaddition , acylation , alkyne , combinatorial chemistry , catalysis , reactivity (psychology) , peptide , polymer chemistry , organic chemistry , biochemistry , medicine , alternative medicine , pathology
Abstract 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.