conette
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Tryptophan copper chelate formation
Hi! Stumbled upon an old article about decarboxylation of tryptophan with resulting tryptamine product. Can't wrap my head around diagram present in it that depicts
tryptophan chelate formation. For some reason it states that 1/2 of Cu2+ ion is attached to tryptophan, but not sure how it is possible. Logically,
carboxyl group gives up its proton and binds to copper and amine group shares its lone pair with it and indeed we need to have 1/2 Cu2+ to keep
molecule neutral, but how?
Can you please help me to understand?
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DraconicAcid
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You get two amino acid anions coordinating to each copper.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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zed
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Ummm. Copper Chromite has potential. It works nicely in the decarboxylation of Nicotinic Acid.
Still, the in-vogue approach to decarboxylating amino acids, seems to be refluxing the Amino-Acid in a ketone, Like Acetophenone. We have an article
somewhere around here, that utilizes peppermint oil as the ketone source.
The original author, as I recall, was someone with the nom-de-plume of "student".
https://www.sciencemadness.org/whisper/viewthread.php?tid=15...
[Edited on 1-5-2025 by zed]
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walruslover69
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Speak of me and I shall appear!
I've always been interested in these metal catalyzed decarboxylations, but have never personally tried one. I recall reading a procedure that
generated the copper tryptophan chelate then carried out the decarboxylation in DMSO. I never had easy access to DMSO so I abandoned the route.
Nonetheless it is very interesting chemistry!
Does anyone have information to share on the the mechanism for how these decarboxylations proceed or why copper seams to be the preferred catalyst?
Why is DMSO the chosen solvent for doing the decarboxylation? is it due to it's solubility characteristics or participate in the reaction?
[Edited on 2-5-2025 by walruslover69]
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chempyre235
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If the OP is in the US, DMSO is readily available OTC, in 99%+ purity from Wal-Mart and Tractor Supply.
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dicyanin
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I remember having tried this procedure many moons ago. The tryptophan copper chelate is easily made, but the tricky part is to extract tryptamine from
the horrible mess that is the post-rxn mixture from heating the copper chelate in DMSO.
sic transit gloria mundi
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Texium
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Thread Moved
4-5-2025 at 06:04 |
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