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Synthesis of oligonucleotides carrying 5′-5′ linkages using copper-catalyzed cycloaddition reactions

AutorAlvira, Margarita; Eritja Casadellà, Ramón
Palabras clavealkyne derivative
copper derivative
azide
oligonucleotide
phosphoramidon
Molecular structure
Fecha de publicación2007
EditorJohn Wiley & Sons
CitaciónChemistry and Biodiversity
ResumenThere is considerable interest in coupling oligonucleotides to molecules and surfaces. Although amino- and thiol-containing oligonucleotides are being successfully used for this purpose, cycloaddition reactions may offer greater advantages due to their higher chemoselectivity and speed. In this study, copper-catalyzed 1,3-dipolar cycloaddition reactions between oligonucleotides carrying azido and alkyne groups are examined. For this purpose, several protocols for the preparation of oligonucleotides carrying these two groups are described. The non-templated chemical ligation of two oligonucleotides via copper-catalyzed [3 + 2] cycloaddition is described. By solid-phase methodology, oligonucleotides carrying 5′-5′ linkages can be obtained in good yields.
Versión del editorDOI: 10.1002/cbdv.200790229
URIhttp://hdl.handle.net/10261/124969
DOI10.1002/cbdv.200790229
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