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1: Chem Biodivers. 2007 Dec;4(12):2798-809.Click here to read Links

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

Alvira M, Eritja R.

Institut de Biologia Molecular de Barcelona-CSIC, CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Josep Samitier 1, E-08028 Barcelona.

There 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.

PMID: 18081090 [PubMed - indexed for MEDLINE]