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Azido-dT Phosphoramidite

Azido-dT Phosphoramidite is an excellent building block for introducing an azide group into an oligo via dT. Oligonucleotides bearing a single nucleosidic azide group can be readily modified with 2-5 equivalents of a tag-alkyne (e.g., a fluorescent dye alkyne). After the addition of complexed Cu(I), complete conversion to the labelled oligo can be achieved typically between 30 min and a few hours. After a simple precipitation step, labelled oligonucleotides can be recovered in high yields. The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction between azides and alkynes to form 1,2,3-triazoles, as reported by Sharpless, is exquisitely regioselective and efficient at even the mildest conditions. The use of this method for DNA modification was somewhat hindered by the fact that copper ions damage DNA, typically yielding strand breaks. As these problems have now been overcome by the use of copper(I)-stabilizing ligands (e.g., tris(benzyltriazolylmethyl)amine, TBTA3), the CuAAC reaction is now increasingly used to functionalize alkyne-modified DNA nucleobases with extremely high efficiency.

References

View all 50 references: Citation Explorer
Fluorescent labeling of RNA and DNA on the Hoogsteen edge using sulfinate chemistry.
Authors: Bassi, Tiziano and Hirlinger, Anastassia and Grayson, Leah and Vantourout, Julien and Toor, Navtej
Journal: RNA (New York, N.Y.) (2023): 1437-1451
Halogen-Bonding Heteroditopic [2]Catenanes for Recognition of Alkali Metal/Halide Ion Pairs.
Authors: Tay, Hui Min and Tse, Yuen Cheong and Docker, Andrew and Gateley, Christian and Thompson, Amber L and Kuhn, Heike and Zhang, Zongyao and Beer, Paul D
Journal: Angewandte Chemie (International ed. in English) (2023): e202214785
Expanding the synthesis of a library of potent glucuronic acid glycodendrons for Dengue virus inhibition.
Authors: Ramírez-López, Pedro and Martínez, Carlos and Merchán, Alejandro and Perona, Almudena and Hernaiz, María J
Journal: Bioorganic chemistry (2023): 106913
Expanding the Toolbox of Target Directed Bio-Orthogonal Synthesis: In Situ Direct Macrocyclization by DNA Templates.
Authors: Chaudhuri, Ritapa and Prasanth, Thumpati and Dash, Jyotirmayee
Journal: Angewandte Chemie (International ed. in English) (2023): e202215245
Hierarchical Self-Assembly of Triphilic Main-Chain-Type Semifluorinated Alternating Graft Copolymers in Aqueous Solution.
Authors: Cheng, Jiannan and Yu, Qing and Tu, Kai and Wang, Jinying and Zhang, Lifen and Cheng, Zhenping
Journal: Macromolecular rapid communications (2023): e2200570
Page updated on March 31, 2025

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50 umoles
100 umoles
Catalog Number
62166217
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Physical properties

Molecular weight

868.93

Solvent

MeCN

Storage, safety and handling

H-phraseH303, H313, H333
Hazard symbolXN
Intended useResearch Use Only (RUO)
R-phraseR20, R21, R22

Storage

Freeze (< -15 °C); Minimize light exposure
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