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AAT Bioquest

FastClick™ 5-TAMRA Alkyne

FastClick™ 5-TAMRA Alkyne contains both the moiety of FastClick (for assisting click efficiency) and 5-TAMRA fluorophore (as the fluorescence tag) for developing 5-TAMRA-based fluorescent probes. It readily reacts with an azido-modified biomolecule under extremely mild conditions. 5-TAMRA is one of the most common orange-red fluorophores used for labeling biomolecules, in particular, for labeling peptides. 5-TAMRA conjugates are widely used in fluorescence-based biological detections such as for developing FRET protease substrates. 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 27 references: Citation Explorer
Monitoring regional astrocyte diversity by cell type-specific proteomic labeling in vivo.
Authors: Prabhakar, Priyadharshini and Pielot, Rainer and Landgraf, Peter and Wissing, Josef and Bayrhammer, Anne and van Ham, Marco and Gundelfinger, Eckart D and Jänsch, Lothar and Dieterich, Daniela C and Müller, Anke
Journal: Glia (2023): 682-703
trans-Cyclooctene- and Bicyclononyne-Linked Nucleotides for Click Modification of DNA with Fluorogenic Tetrazines and Live Cell Metabolic Labeling and Imaging.
Authors: Spampinato, Ambra and Kužmová, Erika and Pohl, Radek and Sýkorová, Veronika and Vrábel, Milan and Kraus, Tomáš and Hocek, Michal
Journal: Bioconjugate chemistry (2023): 772-80
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
Identification and Profiling of Histone Acetyltransferase Substrates by Bioorthogonal Labeling.
Authors: Song, Jiabao and Han, Zhen and Zheng, Y George
Journal: Current protocols (2022): e497
Synthesis and characterization of abscisic acid receptor modulators.
Authors: Vaidya, Aditya S and Park, Sang-Youl and Xing, Zenan and Cutler, Sean R
Journal: Methods in enzymology (2022): 435-470
Page updated on October 4, 2024

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Catalog Number72862
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Physical properties

Molecular weight

738.89

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
The reaction (Green Bar) of FastClick Cy5 Alkyne with coumarin azide 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 alkyne does not effectively react with the coumarin azide substrate.
The reaction (Green Bar) of FastClick Cy5 Alkyne with coumarin azide 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 alkyne does not effectively react with the coumarin azide substrate.
The reaction (Green Bar) of FastClick Cy5 Alkyne with coumarin azide 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 alkyne does not effectively react with the coumarin azide substrate.
Gallery Image 2

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