Fast RNA conjugations on solid phase by strain-promoted cycloadditions

I. Singh, C. Freeman, F. Heaney, A. Madder, J.S. Vyle

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)6633-6639
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number33
DOIs
Publication statusPublished - 07 Sep 2012

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Fingerprint

Dive into the research topics of 'Fast RNA conjugations on solid phase by strain-promoted cycloadditions'. Together they form a unique fingerprint.

Cite this