Mutually Orthogonal Bioconjugation of Vinyl Nucleosides for RNA Metabolic Labeling
Mrityunjay Gupta1, Monika Singha2, Dnyaneshwar B Rasale2
1Department of Chemistry, University of California, Irvine, Irvine, California 92697, United States.
Abstract:
We report a strategy for the orthogonal conjugation of the vinyl nucleosides, 5-vinyluridine (5-VU) and 2-vinyladenosine (2-VA), via selective reactivity with maleimide and tris(2-carboxyethyl)phosphine (TCEP), respectively. The orthogonality was investigated using density functional theory (DFT) and confirmed by reactions with vinyl nucleosides. Further, these chemistries were used to modify RNA for fluorescent cell imaging. These reactions allow for the expanded use of RNA metabolic labeling to study nascent RNA expression within different RNA populations.
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