Azabicyclic vinyl sulfones for residue-specific dual protein labelling.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
28 Apr 2019
28 Apr 2019
Historique:
received:
09
01
2019
accepted:
18
03
2019
entrez:
7
5
2019
pubmed:
7
5
2019
medline:
7
5
2019
Statut:
epublish
Résumé
We have developed [2.2.1]azabicyclic vinyl sulfone reagents that simultaneously enable cysteine-selective protein modification and introduce a handle for further bioorthogonal ligation. The reaction is fast and selective for cysteine relative to other amino acids that have nucleophilic side-chains, and the formed products are stable in human plasma and are moderately resistant to retro Diels-Alder degradation reactions. A model biotinylated [2.2.1]azabicyclic vinyl sulfone reagent was shown to efficiently label two cysteine-tagged proteins, ubiquitin and C2Am, under mild conditions (1-5 equiv. of reagent in NaP
Identifiants
pubmed: 31057781
doi: 10.1039/c9sc00125e
pii: c9sc00125e
pmc: PMC6482879
doi:
Types de publication
Journal Article
Langues
eng
Pagination
4515-4522Références
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