A rational quest for selectivity through precise ligand-positioning in tandem DNA-catalysed Friedel-Crafts alkylation/asymmetric protonation.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
14 Mar 2019
14 Mar 2019
Historique:
received:
11
12
2018
accepted:
22
01
2019
entrez:
19
4
2019
pubmed:
19
4
2019
medline:
19
4
2019
Statut:
epublish
Résumé
Covalent anchorage of a metallic co-factor to a DNA-based architecture is merely the only way to ensure an accurate positioning of a catalytic site within the chiral micro-environment offered by the DNA double helix. Ultimately, it also allows a fine-tuning of the catalytic pocket through simple synthetic modifications of the DNA sequence. Here, we report highly selective copper(ii)-catalysed asymmetric Friedel-Crafts conjugate addition/enantioselective protonation, which is due to a careful positioning of a bipyridine ligand within a DNA framework. Most importantly, this study unveils specific structural features that account for an optimal chirality transfer from the duplex to the Friedel-Crafts adducts.
Identifiants
pubmed: 30996865
doi: 10.1039/c8sc05543b
pii: c8sc05543b
pmc: PMC6429601
doi:
Types de publication
Journal Article
Langues
eng
Pagination
2875-2881Références
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