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Three-Component Bioorthogonal Reactions on Cellular DNA and RNA.
- Source :
-
Bioconjugate chemistry [Bioconjug Chem] 2019 Dec 18; Vol. 30 (12), pp. 2991-2997. Date of Electronic Publication: 2019 Nov 13. - Publication Year :
- 2019
-
Abstract
- Metabolic incorporation of bioorthogonal functional groups into chromatin, followed by copper-free conjugation reactions, often gives low yields due to steric hindrance. Here we report that a cationic Sondheimer diyne derivative "DiMOC" rapidly reacts with azide groups in duplex DNA that are otherwise unreactive toward aliphatic cyclooctynes such as bicyclo[6.1.0]nonyne (BCN). DiMOC reversibly intercalates into duplex DNA and undergoes tandem strain-promoted cross-linking of two different azide groups to give DNA-DiMOC-"X" cross-links, where "X" theoretically represents a fluorescent probe, affinity tag, RNA, protein, carbohydrate, and so forth. As a proof of principle, the metabolic incorporation of azide-modified nucleosides into cellular DNA or RNA, followed by treatment with DiMOC and a fluorescent azide enabled visualization of newly synthesized nucleic acids in whole cells.
Details
- Language :
- English
- ISSN :
- 1520-4812
- Volume :
- 30
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- Bioconjugate chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 31697067
- Full Text :
- https://doi.org/10.1021/acs.bioconjchem.9b00630