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Oligo Modifications List | Oligo Modifications Reference Category
Modification : Coumarin Azide
Reference Catalog Number 26-6726
Category Click Chemistry
Modification Code Cou-N3
5 Prime Y
3 Prime Y
Internal Y
Molecular Weight (mw) 203.15
Technical Info (pdf) PS26-6726.pdf
Catalog NoScalePrice
26-6726-0550 nmol$350.00
26-6726-02200 nmol$350.00
26-6726-011 umol$455.00
26-6726-032 umol$682.50
26-6726-1010 umol$3,640.00
26-6726-1515 umol$4,550.00

Coumarin (7-Hydroxycoumarin)-Azide is a fluorescent dye containing a terminal azide group. Coumarin is also known as umbelliferone. Coumarin is highly fluorescent and pH-sensitive, with an absorbance maximum of 358 nm and an emission maximum of 480 nm; thus it emits in the blue region of the visible spectrum. 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 Coumarin-Azide 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). Because coumarin is effectively quenched if its hydroxyl group is either alkylated or phosphorylated, it is useful in high-throughput screening for enzyme lipases and phosphatases.

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.
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