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Natural Science Forum / Chemistry / Organic Synthesis / May 2005decarboxylation of tyrosine?
I was wondering if the simple heating of Tyrosine to high temp. would decarboxylate it to Tyramine, or if it has to be heated in conc. H2SO4 catalyst. If it does decarboxylate without too many side rxns, could this be applied to other suitable amino acids? Lit. says Tyrosine decomposes at 342-344degC; is this decomposition the decarboxylation? Thanks for all your help. Yes, I bet that by simple heating tyrosine would decarboxylate to tyramine. The only problem is that probably a temperature in excess of 200 ?C will be needed. I suspect that heating in the neat would produce plenty of polymerization and oligomerization. I would try boiling a solution in a solvent with a boiling point between 200 and 250 ?C. Either it decarboxylates or it breaks into pieces...or both. Certainly it is worth trying. Gabriel Tojo Yes, I bet that by simple heating tyrosine would decarboxylate to tyramine. The only problem is that probably a temperature in excess of 200 ?C will be needed. I suspect that heating in the neat would produce plenty of polymerization and oligomerization. I would try boiling a solution in a solvent with a boiling point between 200 and 250 ?C. Either it decarboxylates or it breaks into pieces...or both. Certainly it is worth trying. Gabriel Tojo If my memory serves me correctly, you can simply react Tyrosine with BaOH to get Tyramine. Try reacting tyrosine with BaOH to decarboxolate it. |
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