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Oligo Modifications List | Oligo Modifications Reference Category
Modification : Azide PC NHS
Reference Catalog Number 26-6755
Category Click Chemistry
Modification Code N3-PC N
5 Prime Y
3 Prime Y
Internal Y
Molecular Weight (mw) 85
Technical Info (pdf) PS26-6755.pdf
Catalog NoScalePrice
26-6755-0550 nmol$285.00
26-6755-02200 nmol$285.00
26-6755-011 umol$365.00
26-6755-032 umol$475.00
26-6755-1010 umol$1,248.00
26-6755-1515 umol$1,560.00
Related Modifications
Tetrazine-Sulfo-NHS
TCO-PEG4 NHS
Tetrazine methyl PEG4
Azide C3 3'
Azide PEG4 NHS
DBCO-TEG (5')
DBCO-dT
DBCO PC NHS
DBCO PEG13 NHS
Azide C6 (5')
Azide PC NHS
DBCO-C6 NHS
Azide dT (5')
TCO NHS
Azide-C2 NHS
Tetrazine methyl PC NHS
DBCO PEG4 NHS
DBCO-C2 NHS
Tetrazine-PEG5-NHS

This modification is a post synthesis NHS conjugation to a primary amino group thus an additional modification with an amino group is required. A C6 or C12 amino group can be placed at the 5' or for the 3' end a C3 or C7 amino and for internal positions an amino modified base is used, e.g Amino dT C6.

Click here for a complete list of Click Chemistry Oligo Modifications


Azide PC 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 C3, C6 or C12 for the 5' end or amino C3, C6 or C7 for the 3' end for the ends) or the amino C6 version of the base phosphoramidite (for internal labeling). The Azide C2 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.


Photo Cleavage Protocol

Cleavage occurs by irradiation with near-UV light (300-350 nm, >90% cleavage occurs within 5-25 minutes. Try using a Black Ray XX-15 UV lamp (Ultraviolet Products Inc., San Gabriel, CA) at a distance of 15 cm (emission peak 365 nm, 300 nm cut-off, 1.1 mW intensity at~31 cm).



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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