Fast RNA conjugations on solid phase by strain-promoted cycloadditions

Singh, Ishwar and Freeman, Colin and Madder, Annemieke and Vyle, Joseph S. and Heaney, Frances (2012) Fast RNA conjugations on solid phase by strain-promoted cycloadditions. Organic & Biomolecular Chemistry, 10 (33). pp. 6633-6639. ISSN 1477-0520

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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

Item Type: Article
Additional Information: Organic & Biomolecular Chemistry 2012 Sep 7;10(33):6633-9. Epub 2012 Jul 2. DOI:10.1039/C2OB25628B
Keywords: RNA conjugations; solid phase; strain-promoted cycloadditions; RNA-cyclooctyne;
Academic Unit: Faculty of Science and Engineering > Chemistry
Item ID: 3825
Depositing User: Dr. Frances Heaney
Date Deposited: 21 Aug 2012 15:36
Journal or Publication Title: Organic & Biomolecular Chemistry
Publisher: Royal Society of Chemistry
Refereed: Yes

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