Singh, Ishwar and Freeman, Colin and Madder, Annemieke and Vyle, Joseph S. and Heaney, Frances
Fast RNA conjugations on solid phase by strain-promoted cycloadditions.
Organic & Biomolecular Chemistry, 10 (33).
Strain promoted cycloaddition is presented as a tool for RNA conjugation on the solid phase;
RNA-cyclooctyne conjugates are prepared by cycloaddition to both azide (strain-promoted azide–alkyne
cycloaddition, SPAAC) and nitrile oxide dipoles (strain-promoted nitrile oxide–alkyne cycloaddition,
SPNOAC). The conjugation is compatible with 2′-OMe blocks and with 2′-O-TBDMS protection on the
ribose moieties of the sugar. Nitrile oxide dipoles are found to be more reactive click partners than azides.
The conjugation proceeds within 10 min in aqueous solvents, at room temperature without any metal
catalyst and tolerates dipoles of varying steric bulk and electronic demands, including pyrenyl, coumarin
and dabcyl derivatives
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