I have previously had success with protein modification using EDC/NHS as a method for coupling COOH groups with primary amines.
Now, I’m trying to form a hydrazide group on a small molecule (4-carboxy-TEMPO). In theory, I suspect that the same EDC/NHS method should work to form a hydrazide, using hydrazine(N2H4) as the primary amine, but it hasn’t been successful.
My conditions are 1:4:4 molar ratio of COOH:EDC:NHS:N2H4 in 75mM MES pH 4.5.
Analysis via LC-MS shows no sign of the desired product. Any thoughts/suggestions would be appreciated!
Hi,
I have tried one of such system but with calixarene derivative, where I coupled primary amine of hydrazine with acid of 3-thiophene aceticacid. I used only EDC.HCl in dry acetonitrile. (Solvent has to be dry and reaction should be under inert atmosphere). you can see the paper I have attached here.
Best of luck.
Hi James Purcell . You could try EDC coupling of 4-Aminobenzoic hydrazide to the -COOH.
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