title: An immobilized and reusable Cu(I) catalyst for metal ion-free conjugation of ligands to fully deprotected oligonucleotides through click reaction.
abstract: Chelation of Cu(I) ions to an immobilized hydrophilic tris(triazolylmethyl)amine chelator on a solid support allowed synthesis of RNA oligonucleotide conjugates from completely deprotected alkyne-oligonucleotides. No oligonucleotide strand degradation or metal ion contamination was observed. Furthermore, use of the immobilized copper(I) ion overcame regioselectivity issues associated with strain-promoted copper-free azide-alkyne cycloaddition.
authors.affiliation: Drug Discovery, Alnylam Pharmaceuticals, 300 Third Street, Cambridge, MA 02142, USA.
authors.forename: Laxman
authors.initials: L
authors.lastname: Eltepu
authors.forename: Muthusamy
authors.initials: M
authors.lastname: Jayaraman
authors.forename: Kallanthottathil G
authors.initials: KG
authors.lastname: Rajeev
authors.forename: Muthiah
authors.initials: M
authors.lastname: Manoharan
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D008024:Ligands; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D011137:Polystyrenes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001386:Azides; D002614:Chelating Agents; D007477:Ions; D008024:Ligands; D009841:Oligonucleotides; D011137:Polystyrenes; D003300:Copper