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 and Biomolecular Chemistry, 10 (33). pp. 6633-6639. ISSN 1477-0520

Full content URL: http://dx.doi.org/10.1039/c2ob25628b

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Item Type:Article
Item Status:Live Archive

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 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.

Additional Information:First published online 13 Jun 2012
Keywords:RNA
Subjects:B Subjects allied to Medicine > B200 Pharmacology, Toxicology and Pharmacy
Divisions:College of Science > School of Pharmacy
ID Code:11290
Deposited On:24 Jul 2013 09:22

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