Peer-Reviewed Journal Details
Mandatory Fields
Singh, I;Freeman, C;Madder, A;Vyle, JS;Heaney, F
2012
January
Organic and Biomolecular Chemistry
Fast RNA conjugations on solid phase by strain-promoted cycloadditions
Published
15 ()
Optional Fields
FREE CLICK CHEMISTRY AZIDE-ALKYNE CYCLOADDITION 1,3-DIPOLAR CYCLOADDITION EFFICIENT SYNTHESIS DNA FUNCTIONALIZATION LIGATION POLYMER
10
6633
6639
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.
CAMBRIDGE
1477-0520
10.1039/c2ob25628b
Grant Details