Photoredox-Catalyzed Labeling of Hydroxyindoles with Chemoselectivity (PhotoCLIC) for Site-Specific Protein Bioconjugation.
Bioconjugation
Chemoselectivity
Photoredox Catalysis
Protein Labeling
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
03 07 2023
03 07 2023
Historique:
received:
18
01
2023
pmc-release:
03
07
2024
medline:
29
6
2023
pubmed:
23
5
2023
entrez:
23
5
2023
Statut:
ppublish
Résumé
We have developed a novel visible-light-catalyzed bioconjugation reaction, PhotoCLIC, that enables chemoselective attachment of diverse aromatic amine reagents onto a site-specifically installed 5-hydroxytryptophan residue (5HTP) on full-length proteins of varied complexity. The reaction uses catalytic amounts of methylene blue and blue/red light-emitting diodes (455/650 nm) for rapid site-specific protein bioconjugation. Characterization of the PhotoCLIC product reveals a unique structure formed likely through a singlet oxygen-dependent modification of 5HTP. PhotoCLIC has a wide substrate scope and its compatibility with strain-promoted azide-alkyne click reaction, enables site-specific dual-labeling of a target protein.
Identifiants
pubmed: 37219923
doi: 10.1002/anie.202300961
pmc: PMC10330600
mid: NIHMS1904861
doi:
Substances chimiques
Proteins
0
Azides
0
5-Hydroxytryptophan
C1LJO185Q9
Alkynes
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300961Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM134964
Pays : United States
Organisme : NIGMS NIH HHS
ID : R35 GM136437
Pays : United States
Organisme : NIGMS NIH HHS
ID : R35GM134964
Pays : United States
Organisme : NIGMS NIH HHS
ID : R35GM136437
Pays : United States
Informations de copyright
© 2023 Wiley-VCH GmbH.
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