IF 15
TBTA
Catalog No.: GC45003Purity:>98.00%Synonyms: Tris(benzyltriazolylmethyl)amine
TBTA (tris(benzyltriazolylmethyl)amine) is a tertiary amine containing a 1,2,3-triazole group. TBTA complexes with copper(I) and promotes click reaction catalysis by stabilizing the copper(I) oxidation state.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 510758-28-8
50mgIn Stock
$32.00
1
250mgIn Stock
$57.00
1
500mgIn Stock
$97.00
1
1gIn Stock
$143.00
1
| Pack Size | Price | Availability | Quantity | Action |
|---|---|---|---|---|
| 50mg | $32.00 | In Stock | 1 | |
| 250mg | $57.00 | In Stock | 1 | |
| 500mg | $97.00 | In Stock | 1 | |
| 1g | $143.00 | In Stock | 1 |
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Citations
7 publicationsPublications from researchers using this productIF 14
PMID: 41361996 ↗IF 13
PMID: 38146933 ↗IF 13
PMID: 37471002 ↗IF 12
PMID: 35349929 ↗Description
TBTA (tris(benzyltriazolylmethyl)amine) is a tertiary amine containing a 1,2,3-triazole group[1]. TBTA complexes with copper(I) and promotes click reaction catalysis by stabilizing the copper(I) oxidation state[2]. TBTA is one of the most widely used water-insoluble ligands in copper-catalyzed azide-alkyne cycloaddition (CuAAC)[3].
TBTA Click chemistry is a versatile reaction that can be used for the synthesis of a variety of conjugates. Virtually any biomolecule can be easily labeled with small molecules, such as fluorescent dyes, biotin, etc using the click chemistry method.
TBTA Click chemistry reaction takes place between two components: azide and alkyne (terminal acetylene). Both azido and alkyne groups are nearly never encountered in natural biomolecules. Hence, the reaction is highly bioorthogonal and specific, particularly when using a copper(I) catalyst stabilized by the ligand TBTA.
References:
[1] Alireza Movahedi, et al. One-pot synthesis of TBTA-functionalized coordinating polymers. Reactive and Functional Polymers.2014. 82:1-8.
[2] Kennedy DC, McKay C S, Legault M C B, et al. Cellular consequences of copper complexes used to catalyze bioorthogonal click reactions[J]. Journal of the American Chemical Society, 2011, 133(44): 17993-18001.
[3] Hagmann V, Sommer S, Fabian P, et al. Chemically monoubiquitinated PEX5 binds to the components of the peroxisomal docking and export machinery[J]. Scientific Reports, 2018, 8(1): 16014.
Protocol
This plan only provides a guide, please modify it to meet your specific needs.
1. Calculate the volumes of reagents required for Click chemistry labeling using the table below. Prepare the required stock solutions(see Appendix).
|
Reagent |
Final concentration in the mixture |
Stock solution concentration |
|
Oligonucleotide, alkyne-modified |
Varies (20 — 200 uM) |
Varies |
|
Azide |
1.5 x (oligonucleotide concentration) |
10 mM in DMSO |
|
DMSO |
50 vol % |
— |
|
Ascorbic acid |
0.5 mM |
5 mM in water |
|
Cu-TBTA complex |
0.5 mM |
10 mM in 55 vol % DMSO |
2. Dissolve alkyne-modified oligonucleotide or DNA in water in a pressure-tight vial.
3. Add 2M triethylammonium acetate buffer, pH 7.0, to final concentration 0.2 M.
4. Add DMSO, and vortex.
5. Add azide stock solution (10 mM in DMSO), and vortex.
6. Add the required volume of 5mM Ascorbic Acid Stock solution to the mixture, and vortex briefly.
7. Degass the solution by bubbling inert gas in it for 30 seconds. Nitrogen, argon, or helium can be used.
8. Add the required amount of 10 mM Copper (II)-TBTA Stock in 55% DMSO to the mixture. Flush the vial with inert gas and close the cap.
9. Vortex the mixture thoroughly. If significant precipitation of azide is observed, heat the vial for 3 minutes at 80°C, and vortex.
10. Keep at room temperature overnight.
11. Precipitate the conjugate with acetone (for oligonucleotides) or with ethanol (for DNA). Mix thoroughly and keep at −20 °C for 20 minutes.
To precipitate an oligonucleotide conjugate: add to the mixture at least a 4-fold excess volume of 3% lithium perchlorate in acetone (if the volume of the mixture is large, split in several vials).
To precipitate a DNA conjugate: add to the mixture sodium acetate to a final concentration of 0.3M; add 2.5 volumes of ethanol (or 0.8 volumes of isopropanol).
12. Centrifuge at 10000 rpm for 10 minutes.
13. Discard the supernatant. Wash the pellet with acetone (1 mL), centrifuge at 10000 rpm for 10 minutes.
14. Discard the supernatant, dry the pellet, and purify the conjugate by RP-HPLC or PAGE.
Appendix. Preparation of stock solutions of the reagents used for click-chemistry labeling and conjugation.
|
5 mM Ascorbic Acid Stock |
|
|
Preparation |
Dissolve 18 mg of ascorbic acid in 20 mL of distilled water |
|
Storage |
Ascorbic acid is readily oxidized by air. The solution is stable for one day. Use fresh preparations |
|
10 mM Copper (II)-TBTA Stock in 55% DMSO |
|
|
Preparation |
Dissolve 50 mg of copper (II) sulfate pentahydrate in 10 mL of distilled water. Dissolve 116 mg of TBTA ligand in 11 mL of DMSO. Mix two solutions |
|
Storage |
Store at room temperature. The solution is stable for years |
|
2M Triethylammonium Acetate Buffer, pH 7.0 |
|
|
Preparation |
Mix 2.78 mL of triethylamine with 1.14 mL of acetic acid. Add water to 10 mL volume, and adjust pH to 7.0 |
|
Storage |
Store at room temperature. The solution is stable for years |
Product Documents
Purity:>98.00%Appearance:A solid
Chemical Properties
CAS No.
510758-28-8
Synonyms
Tris(benzyltriazolylmethyl)amine
SMILES
C1(CN(CC2=CN(CC3=CC=CC=C3)N=N2)CC4=CN(CC5=CC=CC=C5)N=N4)=CN(CC6=CC=CC=C6)N=N1
Molecular Formula
C30H30N10
Molecular Weight
530.6
Solubility
DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.
CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility
g/mol
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