Synthesis of oligonucleotides carrying 5'-5' linkages using copper-catalyzed cycloaddition reactions.
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.
Alvira
Margarita
M
Institut de Biologia Molecular de Barcelona-CSIC, CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Josep Samitier 1, E-08028 Barcelona.
Eritja
Ramon
R
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D003300:Copper / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry
D003432:Cross-Linking Reagents; D009841:Oligonucleotides; D003300:Copper