Decarboxylation of l-alanine, various musings

nyarlothotep · Tue Apr 19, 2005 11:10 am

Good man.

Something is a tad incongrous tho.....assuming the same type of mechanism to be in action with other reports of aromatic ketone-induced decarboxylation, (once again, see Tryptophan-tryptamine notes) then what is the difference?
Is it the aromatic ring on the to-be-decarboxylated substrate?

because the article that the kind user found suggests that choice of ketone has a significant effect upon the final product of the decarboxylation attempt

Also referenced in that article previously mentioned are a few other experiments in the short chain aminoacids.....primarily looking towards deamination, but could provide some vital clues as to how this works on short chained aminos.

Funny thing is, the way Swin sees it, is that we're looking at a crude duplicate of the mechanisms used in vivo to selectively decarboxylate anything. Smile

Barring further journal accounts, this should be experimented with, using a broad range of ketones. It looks viable. And the fact that l-alanine doesn't have one of those sulfer atoms or chain-end amino groups is a big plus, because if you noticed, the yields went to shit when there was anything other than a carbon chain, slightly ameliorated by the atom's inclusion into a ring. Probably due to the atom's ability to pull charge.

random train of thought starts here....
Seeing as all of the ketones used or suggested as swin has read thus far are aromatic, perhaps the aromaticity itself is enough of a charge donor to stabilize the more stable amino acids (such as the cyclical ones, tryptamine being the base reference....) whereas the non-aromatic aminos might need a more significant charge donor to make up for their inherent instability.....maybe an attempt using a non-substituted aromatic ketone on alanine or isoleucine/leucine would result in production of CO₂ , NH₃ and the corresponding alkane......
this is getting interesting.

IndoleAmine · Dreamreader Deluxe

Hey Java: this japanese article is probably also quite interesting in the context of the Akabori rxn - what do you think?

(sorry to interrupt your train, nyo.! Laughing

)

java · Consumer

I misplaced my response only because the reply applied to more than one thread

.............as was posted here,

http://synthetikal.com/synthforum/viewtopic.php?p=4346#4346

as for the decarboxylation of phenylalanine WizardX provided this at WD and a reference link....