| Size | Price | Stock | Qty |
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| 10mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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BTTAA, a Cu(I)-stabilizing ligand, is a next-generation, water-soluble ligand for the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) that dramatically accelerates reaction rates and suppresses cell cytotoxicity. The biocompatibility and fast kinetics of BTTAA are advancements from water-insoluble TBTA and are desirable for bio conjugation in diverse chemical biology experiments. References: Lanthanide tags for site-specific ligation to an unnatural amino acid and generation of pseudocontact shifts inproteins. Bioconjug Chem. 2013 Feb 20;24(2):260-8.
| Targets |
Copper(I) ion stabilizing ligand / catalyst [1]
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|---|---|
| ln Vitro |
BTTAA is a ligand that stabilizes Cu(I). Cu-BTTAA outperformed Cu-THPTA or Cu-TBTA as a catalyst when applied to the Glu18AzF mutant of ubiquitin, which was used as a model system with C3-Tm3+ and C4-Tm3+. Compared to THPTA (tris[(1-hydroxy-propyl-1H-1,2,3-triazol-4-yl)methyl]amine) and TBTA (tris[(1-benzyl-1H-1, 2,3-triazol-4-yl)methyl]amine), BTTAA has been demonstrated to perform better[1].
BTTAA was used as a Cu(I)-stabilizing ligand to catalyze the click ligation reaction between alkyne-bearing lanthanide tags (C3, C4) and the unnatural amino acid p-azido-L-phenylalanine (AzF) incorporated into various proteins (e.g., ubiquitin, p75 ICD, sortase A). [1] When tested alongside other Cu(I)-stabilizing ligands THPTA and TBTA in the ligation reaction using the ubiquitin Glu18AzF mutant with C3-Tm³⁺ and C4-Tm³⁺ tags, BTTAA performed significantly better, yielding higher ligation efficiencies. [1] The presence of a C-terminal His₆ tag on the target protein was found to reduce ligation yields with BTTAA, presumably due to competition between the histidine side chains and BTTAA for binding copper ions. [1] |
| References | |
| Additional Infomation |
BTTAA (2-[4-[(bis[(1-tert-butyl-1H-1,2,3-triazol-4-yl)methyl]amino)methyl]-1H-1,2,3-triazol-1-yl]acetic acid) is a copper-binding ligand used to stabilize Cu(I) ions for Cu(I)-catalyzed azide-alkyne cycloaddition reactions (Click Chemistry). [1]
In the context of site-specific lanthanide tagging of proteins for paramagnetic nuclear magnetic resonance spectroscopy, BTTAA has been found to achieve higher linkage yields than THPTA and TBTA, especially under conditions of greater steric hindrance near the protein surface. [1] The standard ligation protocol using BTTAA consists of 1 mM BTTAA, 0.2 mM CuSO₄ and 5 mM sodium ascorbate dissolved in 50 mM HEPES buffer (pH 7.5), and the reaction is carried out at room temperature for 16 hours. [1] For proteins susceptible to aggregation of ascorbic acid oxidation byproducts (e.g., p75 ICD, sortase A), the ligation reaction using BTTAA requires the addition of 0.5 mM glycerol and 5 mM aminoguanidine to improve stability and yield. [1] The order of addition is crucial: adding the reducing agent sodium ascorbate after adding the Cu(II) solution containing BTTAA results in a higher yield than adding the pre-incubated mixture of all components. [1] |
| Molecular Formula |
C19H30N10O2
|
|---|---|
| Molecular Weight |
430.5073
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| Exact Mass |
430.255
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| CAS # |
1334179-85-9
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| PubChem CID |
56655929
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| Appearance |
White to off-white solid powder
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| Melting Point |
115.5 - 116.5 °C
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| LogP |
1.258
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
10
|
| Heavy Atom Count |
31
|
| Complexity |
574
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
MGQYHUDOWOGSQI-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C19H30N10O2/c1-18(2,3)28-11-15(21-24-28)8-26(7-14-10-27(23-20-14)13-17(30)31)9-16-12-29(25-22-16)19(4,5)6/h10-12H,7-9,13H2,1-6H3,(H,30,31)
|
| Chemical Name |
2-[4-[[bis[(1-tert-butyltriazol-4-yl)methyl]amino]methyl]triazol-1-yl]acetic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~5 mg/mL (~11.61 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 50 mg/mL (116.14 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3228 mL | 11.6141 mL | 23.2283 mL | |
| 5 mM | 0.4646 mL | 2.3228 mL | 4.6457 mL | |
| 10 mM | 0.2323 mL | 1.1614 mL | 2.3228 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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