Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 45, Pages 19940-19944Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202009408
Keywords
acylation; click chemistry; peptides; rearrangements; silver
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Funding
- National Natural Science Foundation of China (NNSFC) [21877116, 21702217]
- National Science & Technology Major Project Key New Drug Creation and Manufacturing Program of China [2018ZX09711002-006, 2019ZX09721001]
- Shanghai-Technology Innovation Action Plan [18JC1415300]
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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.
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