CuAAC (Cu catalyzed azide-alkyne cycloadition) product and TBTA has similar Rf values. Hence, it id hard to isolate product using column/prep TLC. Any suggestions to remove TBTA will be greatly appreciated.
Thanks in advance.
What is TBTA? It really depends if the product is the final product or can you take it for subsequent reaction before purification.
You can try precipitation (for oligonucleotides- either acetone, 1M lithium or sodium perchlorate in acetone (more efficient) or ether). Or you can try acidic resin if it does not interfere with your substrate.
I guess, washing the organic layer with any aq Cu(I)X solution can remove it since TBTA can form the complex with Cu(I).
Eugene Yang : TBTA is Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine, a commonly used ligand to stabilize Cu(1) state in click reaction. It is my final product which is a macrocycle which needs to be pure.
Mikhail Nekrasov : Thank you for your suggestion. Does TBTA precipitate with the above mentioned method?
Yalagala Ravi shekar : thanks for the suggestion. However, TBTA was used as a ligand for Cu(1) in my CuAAC reaction. First washing step of my reaction was to remove Cu from mixture by washing with EDTA/NH3. After this, TBTA remains in the organic layer with my product which has caused the problem. Hence, I can not separate TBTA-Cu complex from my product, as both remain in the organic layer. Any suggestions to improve my washing steps further?
I greatly appreciate all your help.
No, oligonucleotides and their derivatives precipitate (though better to centrifuge the mixture), while TBTA remains in solution and can be filtered off. Not sure about proteins or other stuff, that you'll need to look up if you need to.
Resin in this case would be a weak cation exchange resin, but once again, it would only work is your substrate in not basic.
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