Manipulating the Click Reactivity of Dibenzoazacyclooctynes: From Azide Click Component to Caged Acylation Reagent by Silver Catalysis.
Angew Chem Int Ed Engl
; 59(45): 19940-19944, 2020 11 02.
Article
in En
| MEDLINE
| ID: mdl-32697885
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.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Silver
/
Azides
/
Alkynes
/
Click Chemistry
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2020
Document type:
Article
Affiliation country:
China