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Synthesis of Oligonucleotides Carrying 5′‐5′ Linkages Using Copper‐Catalyzed Cycloaddition Reactions
Author(s) -
Alvira Margarita,
Eritja Ramon
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790229
Subject(s) - oligonucleotide , cycloaddition , chemistry , chemoselectivity , combinatorial chemistry , catalysis , copper , coupling reaction , alkyne , 1,3 dipolar cycloaddition , organic chemistry , dna , biochemistry
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.