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Issue 33, 2012
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Fast RNA conjugations on solid phase by strain-promoted cycloadditions

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Abstract

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 oxidealkyne 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.

Graphical abstract: Fast RNA conjugations on solid phase by strain-promoted cycloadditions

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Publication details

The article was received on 27 Mar 2012, accepted on 12 Jun 2012 and first published on 13 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25628B
Citation: Org. Biomol. Chem., 2012,10, 6633-6639
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    Fast RNA conjugations on solid phase by strain-promoted cycloadditions

    I. Singh, C. Freeman, A. Madder, J. S. Vyle and F. Heaney, Org. Biomol. Chem., 2012, 10, 6633
    DOI: 10.1039/C2OB25628B

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