title: Fast RNA conjugations on solid phase by strain-promoted cycloadditions.
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.
authors: Department of Chemistry, NUI Maynooth, Maynooth, Republic of Ireland. ishwar.singh@strath.ac.uk
authors: Ishwar
authors: I
authors: Singh
authors: Colin
authors: C
authors: Freeman
authors: Annemieke
authors: A
authors: Madder
authors: Joseph S
authors: JS
authors: Vyle
authors: Frances
authors: F
authors: Heaney
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001483:Base Sequence; D057930:Click Chemistry / Q000191:economics / Q000379:methods; D061565:Cycloaddition Reaction / Q000191:economics / Q000379:methods*; D009570:Nitriles / Q000737:chemistry; D010087:Oxides / Q000737:chemistry; D012313:RNA / Q000737:chemistry*; D013997:Time Factors
chemical_list: D000480:Alkynes; D001386:Azides; D009570:Nitriles; D010087:Oxides; C042001:1-octyne; D012313:RNA