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AAT Bioquest

FastClick™ 6-TAMRA Azide

FastClick™ 6-TAMRA Azide contains both the CAG moiety of FastClick (for assisting click efficiency) and 6-TAMRA fluorophore (as the fluorescence tag) for developing 6-TAMRA-based fluorescent probes. 6-TAMRA is one of the most widely used orange fluorophores, in particular, for labeling oligonucleotides. 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 7 references: Citation Explorer
Divergent Synthesis of Ultrabright and Dendritic Xanthenes for Enhanced Click-Chemistry-Based Bioimaging.
Authors: Montiel, Luis and Spada, Fabio and Crisp, Antony and Serdjukow, Sascha and Carell, Thomas and Frischmuth, Thomas
Journal: Chemistry (Weinheim an der Bergstrasse, Germany) (2023): e202202633
N-Terminal selective modification of peptides and proteins using 2-ethynylbenzaldehydes.
Authors: Deng, Jie-Ren and Lai, Nathanael Chun-Him and Kung, Karen Ka-Yan and Yang, Bin and Chung, Sai-Fung and Leung, Alan Siu-Lun and Choi, Man-Chung and Leung, Yun-Chung and Wong, Man-Kin
Journal: Communications chemistry (2020): 67
Maleimide-Based Chemical Proteomics for Quantitative Analysis of Cysteine Reactivity.
Authors: McConnell, Evan W and Smythers, Amanda L and Hicks, Leslie M
Journal: Journal of the American Society for Mass Spectrometry (2020)
The application of a novel, cell permeable activity-based probe for the detection of cysteine cathepsins.
Authors: Hughes, Caroline S and Shaw, George and Burden, Roberta E and Scott, Christopher J and Gilmore, Brendan F
Journal: Biochemical and biophysical research communications (2016): 444-50
Nucleic acid sensing by an orthogonal reporter system based on homo-DNA.
Authors: Stoop, Matthias and Désiron, Camille and Leumann, Christian J
Journal: Artificial DNA, PNA & XNA (2013): 28-33
Page updated on October 22, 2024

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Catalog Number72713
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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.

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