Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
03 06 2022
03 06 2022
Historique:
pubmed:
20
5
2022
medline:
7
6
2022
entrez:
19
5
2022
Statut:
ppublish
Résumé
A convergent synthesis provided nearly perfect τ-ADP-ribosylated histidine isosteres (His*-τ-ADPr) via a copper(I)-catalyzed cycloaddition between an azido-ADP-ribosyl analogue and an oligopeptide carrying a propargyl glycine. Both α- and β-configured azido-ADP-ribosyl analogues have been synthesized. The former required participation of the C-2 ester functionality during glycosylation, while the latter was obtained in high stereoselectivity from an imidate donor with a nonparticipating
Identifiants
pubmed: 35587229
doi: 10.1021/acs.orglett.2c01300
pmc: PMC9171823
doi:
Substances chimiques
Histidine
4QD397987E
Adenosine Diphosphate
61D2G4IYVH
Copper
789U1901C5
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
3776-3780Références
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