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Kurzfassung

Labeled oligonucleotides are used in research and for diagnostic, therapeutic and industrial applications. Researchers from the DKFZ and the Heidelberg University developed a fast method for post-synthetic multiple orthogonal labeling of oligonucleotides by combining the inverse Diels-Alder reaction with the well-known copper-catalyzed azide-alkyne cycloaddition.

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Hintergrund

Labeled oligonucleotides are used in research and for diagnostic, therapeutic and industrial applications. Current labeling methods require excess of fluorescent dye and multiple reaction and purification steps. In order to overcome these disadvantages, a fast method for post-synthetic multiple orthogonal labeling of oligonucleotides was developed by combining the inverse Diels-Alder reaction (DARinv) with the well-known copper-catalyzed azide-alkyne cycloaddition (CuAAC).

A preferred embodiment involves the reaction of an N3-reactive group as well as dienophilemodified oligonucleotide (RNA or DNA) with an N3-modified label via a CuAAC reaction as well as a tetrazine-label via an inverse Diels-Alder reaction.

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Lösung

Combining the inverse Diels-Alder reaction (DARinv) with the well-known copper-catalyzed azide-alkyne cycloaddition (CuAAC) to make a fast method for post-synthetic multiple orthogonal labeling of oligonucleotides.

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Vorteile

In comparison with known technologies for postsynthetic multiple orthogonal labeling, the combination of the inverse Diels-Alder reaction with the CuAAC offers the following advantages:

• one step reaction
• no intermediate purification steps necessary
• no side reactions
• fast and cost-effective

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Anwendungsbereiche

The method can be used for research, biotechnology, diagnostic, and therapeutic applications. The technology allows the modification of oligonucleotides with a multitude of labels such as: fluorescent dyes, small molecules, peptides, antibodies, affinity tags, and other biomolecules.