Postsynthetic DNA Modification through the Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction
Philipp M. E. Gramlich Dipl.-Chem.
Center for Integrative Protein Science at the Department of Chemistry and Biochemistry, Ludwigs-Maximilians-University, Butenandtstrasse 5–13, 81377 Munich (Germany), Fax: (+49) 89-2180-77756
BASECLICK GmbH, Bahnhofstrasse 9–15, 82327 Tutzing (Germany) http://www.baseclick.eu
Search for more papers by this authorChristian T. Wirges Dipl.-Chem.
Center for Integrative Protein Science at the Department of Chemistry and Biochemistry, Ludwigs-Maximilians-University, Butenandtstrasse 5–13, 81377 Munich (Germany), Fax: (+49) 89-2180-77756
Search for more papers by this authorAntonio Manetto Dr.
Center for Integrative Protein Science at the Department of Chemistry and Biochemistry, Ludwigs-Maximilians-University, Butenandtstrasse 5–13, 81377 Munich (Germany), Fax: (+49) 89-2180-77756
BASECLICK GmbH, Bahnhofstrasse 9–15, 82327 Tutzing (Germany) http://www.baseclick.eu
Search for more papers by this authorThomas Carell Prof. Dr.
Center for Integrative Protein Science at the Department of Chemistry and Biochemistry, Ludwigs-Maximilians-University, Butenandtstrasse 5–13, 81377 Munich (Germany), Fax: (+49) 89-2180-77756
Search for more papers by this authorPhilipp M. E. Gramlich Dipl.-Chem.
Center for Integrative Protein Science at the Department of Chemistry and Biochemistry, Ludwigs-Maximilians-University, Butenandtstrasse 5–13, 81377 Munich (Germany), Fax: (+49) 89-2180-77756
BASECLICK GmbH, Bahnhofstrasse 9–15, 82327 Tutzing (Germany) http://www.baseclick.eu
Search for more papers by this authorChristian T. Wirges Dipl.-Chem.
Center for Integrative Protein Science at the Department of Chemistry and Biochemistry, Ludwigs-Maximilians-University, Butenandtstrasse 5–13, 81377 Munich (Germany), Fax: (+49) 89-2180-77756
Search for more papers by this authorAntonio Manetto Dr.
Center for Integrative Protein Science at the Department of Chemistry and Biochemistry, Ludwigs-Maximilians-University, Butenandtstrasse 5–13, 81377 Munich (Germany), Fax: (+49) 89-2180-77756
BASECLICK GmbH, Bahnhofstrasse 9–15, 82327 Tutzing (Germany) http://www.baseclick.eu
Search for more papers by this authorThomas Carell Prof. Dr.
Center for Integrative Protein Science at the Department of Chemistry and Biochemistry, Ludwigs-Maximilians-University, Butenandtstrasse 5–13, 81377 Munich (Germany), Fax: (+49) 89-2180-77756
Search for more papers by this authorGraphical Abstract
Labeling of oligonucleotides is of paramount importance for DNA-based nanotechnology and diagnostic applications. The copper-catalyzed reaction of azides with alkynes is currently revolutionizing the way in which these labeled oligonucleotides are synthesized. TBAF=tetrabutylammoniumfluoride, TIPS=triisopropylsilyl, TMS=trimethylsilyl.
Abstract
The attachment of labels onto DNA is of utmost importance in many areas of biomedical research and is valuable in the construction of DNA-based functional nanomaterials. The copper(I)-catalyzed Huisgen cycloaddition of azides and alkynes (CuAAC) has recently been added to the repertoire of DNA labeling methods, thus allowing the virtually unlimited functionalization of both small synthetic oligonucleotides and large gene fragments with unprecedented efficiency. The CuAAC reaction yields the labeled polynucleotides in very high purity after a simple precipitation step. The reviewed technology is currently changing the way in which functionalized DNA strands are generated cost-efficiently in high quality for their application in molecular diagnostics systems and nanotechnological research.
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