Expanding the Scope of RNA Metabolic Labeling with Vinyl Nucleosides and Inverse Electron-Demand Diels-Alder Chemistry.
Journal
ACS chemical biology
ISSN: 1554-8937
Titre abrégé: ACS Chem Biol
Pays: United States
ID NLM: 101282906
Informations de publication
Date de publication:
16 08 2019
16 08 2019
Historique:
pubmed:
17
7
2019
medline:
4
1
2020
entrez:
17
7
2019
Statut:
ppublish
Résumé
Optimized and stringent chemical methods to profile nascent RNA expression are still in demand. Herein, we expand the toolkit for metabolic labeling of RNA through application of inverse electron demand Diels-Alder (IEDDA) chemistry. Structural examination of metabolic enzymes guided the design and synthesis of vinyl-modified nucleosides, which we systematically tested for their ability to be installed through cellular machinery. Further, we tested these nucleosides against a panel of tetrazines to identify those which are able to react with a terminal alkene, but are stable enough for selective conjugation. The selected pairings then facilitated RNA functionalization with biotin and fluorophores. We found that this chemistry not only is amenable to preserving RNA integrity but also endows the ability to both tag and image RNA in cells. These key findings represent a significant advancement in methods to profile the nascent transcriptome using chemical approaches.
Identifiants
pubmed: 31310712
doi: 10.1021/acschembio.9b00079
pmc: PMC8061575
mid: NIHMS1692386
doi:
Substances chimiques
Heterocyclic Compounds, 1-Ring
0
Nucleosides
0
Vinyl Compounds
0
RNA
63231-63-0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
1698-1707Subventions
Organisme : NIGMS NIH HHS
ID : DP2 GM119164
Pays : United States
Organisme : NIMH NIH HHS
ID : R21 MH113062
Pays : United States
Organisme : NCATS NIH HHS
ID : UL1 TR001414
Pays : United States
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