Propargyl NHS Oligo Modification
Propargyl-NHS ester allows the introduction of an active alkyne group to amino-modified oligonucleotides. Usually, this functional group is conjugated to the 5'- or 3'-end, as well as to internal positions. First, the oligonucleotide is synthesized containing a modifier group with a primary amino group and a linker group. In general, amino C3, C6, C12 or other PEG linker groups are added to the 5' end, and amino C3, C6 or C7 groups to the 3' end. The Propargyl NHS ester is then post-synthetically attached to the amino group. The presence of the alkyne group allows the use of "Click Chemistry" (a [3+2] cycloaddition reaction between alkynes and azides, using copper (I) iodide as a catalyst) to conjugate the alkyne-modified oligo to a terminal azide-modified oligonucleotide with extremely high regioselectivity and efficiency (1,2). The use of various azide modifiers allows the preparation of the azide-modified oligonucleotides. Click chemistry also enables the formation of cyclic oligonucleotides under different biophysical and biological conditions. These types of reactions can also be used in-vivo since cyclic oligonucleotides are known to be very stable in serum for up to several days.
Product Information
Propargyl NHS Oligo Modification
-20°C To -70°C
Oligonucleotides are stable in solution at 4°C for up to 2 weeks. Properly reconstituted material stored at -20°C should be stable for at least 6 months. Dried DNA (when kept at -20°C) in a nuclease-free environment should be stable for years.
References/Citations:
- Huisgen, R. Angew. Chem. Int. Ed. (1963), 2: 565-568.
- Rostovtsev, V.V., Green, L.G., Fokin, V.V., Sharpless, K.B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective Ligation of Azides and Terminal Alkynes. Angew. Chem. Int. Ed. (2002), 41: 2596-2599.
- Kumar, R., El-Sagheer, A., Tumpane, J., Lincoln, P., Wilhelmsson, L.M., Brown, T. Template-Directed Oligonucleotide Strand Ligation, Covalent Intramolecular DNA Circularization and Catenation Using Click Chemistry. J. Am. Chem. Soc. (2007), 129: 6859-6864.
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