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Oligo Modifications List | Oligo Modifications Reference Category
Modification : Azide-C4 NHS (butyrate)
Reference Catalog Number 26-6922
Category Click Chemistry
Modification Code N3-C4 N
5 Prime Y
3 Prime Y
Internal Y
Molecular Weight (mw) 113.12
Technical Info (pdf) PS26-6922.pdf
Catalog NoScalePrice
26-6922-0550 nmol$120.00
26-6922-02200 nmol$120.00
26-6922-011 umol$156.00
26-6922-032 umol$234.00
26-6922-1010 umol$1,248.00
26-6922-1515 umol$1,560.00
Related Modifications
Alkyne C8 dT
Azide C3 3'
DBCO-TEG (5')
Alkyne- Serinol
DBCO-dT
Alkyne C8 dC
Propargyl-5-Me-dC(3')
Azide dT (5')
DBCO-C2 NHS
Halotag Conjugation Bromohexyl (5')
Azide-C2 NHS
Azide-C4 NHS (butyrate)
Alkyne-C2 NHS
BCN-1 (bi cyclooctyne)
DBCO-sulfo NHS
Azide C6 (5')

Azidobutyrate NHS ester can be used to introduce an active azide group to an amino-modified oligonucleotide. Introduction can be done at either the 5'- or 3'-end, or internally. To do this, the oligo first must be synthesized with a primary amino functional group modification, e.g Amino C6 for the 5' end or amino C7 for the 3' end for the ends) or the amino C6 version of the base phosphoramidite (for internal labeling). The Azidobutyrate NHS ester is then manually attached to the oligo through the amino group in a separate reaction post-synthesis. The presence of the azide allows the user to use "Click Chemistry" (a [3+2] cycloaddition reaction between alkynes and azides, using copper (I) iodide as a catalyst) to conjugate the azide-modified oligo to a terminal alkyne-modified oligo with extremely high regioselectivity and efficiency (1,2). Preparation of the alkyne-modified oligo can be achieved using the 5’-Hexynyl modifier (see its respective tech sheet for details). Click chemistry can be used to form short, cyclic oligos that can be used as research tools in various biophysical and biological studies (3). In particular, they have considerable potential for in vivo work, as cyclic oligos are known to be very stable in serum for up to several days.




References
1. Huisgen, R. Angew. Chem. Int. Ed. (1963), 2: 565-568.
2. 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.
3. 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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