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AAT Bioquest

FastClick™ 5-TAMRA Azide

FastClick™ 5-TAMRA Azide contains both the CAG moiety of FastClick (for assisting click efficiency) and 5-TAMRA fluorophore (as the fluorescence tag) for developing 5-TAMRA-based fluorescent probes. 5-TAMRA azide is one of the most widely used orange fluorophores, in particular, for labeling alkyne-modified peptides and other small biomolecules. It has almost the identical fluorescence spectra to Alexa Fluor 546, a rhodamine analog. FastClick™ reagents have been developed by the scientists of AAT Bioquest for enhancing the yield and reaction speed of copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. They contain a copper-chelating ligand that significantly stabilizes the Cu(I) oxidation state and thus accelerates the click reaction. They do not require the use of an external copper-chelator (such as the common THPTA or BTTAA). The high concentration of copper chelators is known to have a detrimental effect on DNA/RNA, thus causing biocompatibility issues. The introduction of a copper-chelating moiety at the reporter molecule allows for a dramatic raise of the effective Cu(I) concentration at the reaction site and thus accelerates the reaction. Under extremely mild conditions the FastClick™ azides and alkynes react much faster in high yield compared to the corresponding conventional CuAAC reactions. Click chemistry was developed by K. Barry Sharpless as a robust and specific method of ligating two molecules together. Two important characteristics make click chemistry attractive for assembling biomolecules. First, click reactions are bio-orthogonal, thus the click chemistry-functionalized biomolecules would not react with the natural biomolecules that lack a clickable functional group. Second, the reactions proceed with ease under mild conditions, such as at room temperature and in aqueous media.

References

View all 5 references: Citation Explorer
Direct and specific binding of cholesterol to the mitochondrial translocator protein (TSPO) using PhotoClick cholesterol analogue.
Authors: Georges, Elias and Sottas, Chantal and Li, Yuchang and Papadopoulos, Vassilios
Journal: Journal of biochemistry (2021): 239-243
Profiling and Validation of Live-Cell Protein Methylation with Engineered Enzymes and Methionine Analogues.
Authors: Weiss, Nicole and Seneviranthe, Chamara and Jiang, Ming and Wang, Ke and Luo, Minkui
Journal: Current protocols (2021): e213
New chemical tools for probing activity and inhibition of the NAD+-dependent lysine deacylase sirtuin 2.
Authors: Swyter, Sören and Schiedel, Matthias and Monaldi, Daria and Szunyogh, Sándor and Lehotzky, Attila and Rumpf, Tobias and Ovádi, Judit and Sippl, Wolfgang and Jung, Manfred
Journal: Philosophical transactions of the Royal Society of London. Series B, Biological sciences (2018)
Liposome functionalization with copper-free "click chemistry".
Authors: Oude Blenke, Erik and Klaasse, Gruson and Merten, Hannes and Plückthun, Andreas and Mastrobattista, Enrico and Martin, Nathaniel I
Journal: Journal of controlled release : official journal of the Controlled Release Society (2015): 14-20
Development of clickable active site-directed photoaffinity probes for γ-secretase.
Authors: Crump, Christina J and am Ende, Christopher W and Ballard, T Eric and Pozdnyakov, Nikolay and Pettersson, Martin and Chau, De-Ming and Bales, Kelly R and Li, Yue-Ming and Johnson, Douglas S
Journal: Bioorganic & medicinal chemistry letters (2012): 2997-3000
Page updated on November 9, 2024

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Catalog Number72712
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Physical properties

Molecular weight

642.72

Solvent

DMSO

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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Gallery Image 1
The reaction (Green Bar) of FastClick Cy5 Azide with coumarin alkyne occurs under extremely mild conditions (e.g., [Azide] = 0.02 mM, [Alkyne] = 0.02 mM, [CuSO4] = 0.02 mM, [Sodium Ascorbate] = 5 mM, in 100 mM HEPES) under which the common Cy5 azide does not effectively react with the coumarin alkyne substrate.

Alternative formats