Control of RNA with quinone methide reversible acylating reagents.
Journal
Organic & biomolecular chemistry
ISSN: 1477-0539
Titre abrégé: Org Biomol Chem
Pays: England
ID NLM: 101154995
Informations de publication
Date de publication:
06 10 2021
06 10 2021
Historique:
pubmed:
17
9
2021
medline:
18
3
2022
entrez:
16
9
2021
Statut:
epublish
Résumé
Caging RNA by polyacylation (cloaking) has been developed recently as a simple and rapid method to control the function of RNAs. Previous approaches for chemical reversal of acylation (uncloaking) made use of azide reduction followed by amine cyclization, requiring ∼2-4 h for the completion of cyclization. In new studies aimed at improving reversal rates and yields, we have designed novel acylating reagents that utilize quinone methide (QM) elimination for reversal. The QM de-acylation reactions were tested with two bioorthogonally cleavable motifs, azide and vinyl ether, and their acylation and reversal efficiencies were assessed with NMR and mass spectrometry on model small-molecule substrates as well as on RNAs. Successful reversal both with phosphines and strained alkenes was documented. Among the compounds tested, the azido-QM compound A-3 displayed excellent de-acylation efficiency, with
Identifiants
pubmed: 34528657
doi: 10.1039/d1ob01713f
pmc: PMC8609948
mid: NIHMS1755557
doi:
Substances chimiques
Indolequinones
0
quinone methide
138230-21-4
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Langues
eng
Sous-ensembles de citation
IM
Pagination
8367-8376Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM127295
Pays : United States
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