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tr41414
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Nice reference: http://www.jbc.org/cgi/reprint/62/3/725
 seems there is no easy way to tyramine with high yield... have tried gliceryn and
doesn't seem to do anything but dissolve tyrosine... it was only 1 min run and temp was around 250C, then it starts to boil... the funny thing is that
the thermomether, when removed from testtube does fume a lot (now that i think it may be from water in air and glycerin -> it's used as artificial
fog for special effect  ) and smelled of burned peanuts which was probably
acrolein (wow, a bit toxic)...
Hmm... the biosynthesis sounds like a fun project, but ordinary Saccharomyces cerevisiae (according to www.biochemj.org/bj/069/0210/0690210.pdf) only produce tyrosol, so one would probably have to use some kind of lactic acid bacteria (which can be
found in certain "bioactive" foods  )...
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smuv
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And I point out once again...if you plan to make the nitrile...it can be done in one step from the amino acid with TCCA under very mild conditions
with high yields. There is no need to decarboxylate.
see Synlett 2004: 2180-2184
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dr. nick
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@smuv:
interesting thing, too - read about it with phenylalanine, but do you know any possibility to separate the product without vakuum destillation?
btw.: on more dumb question what is the nitrile of tyrosine? or maybe even arginin? forgive my ignorance, i just don't get it ...
thanks!
of course you can well i couldn\'t before
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smuv
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Based upon the synlett procedure referenced earlier, I would say that the crude ether extracted product should be pure enough to proceed forward with;
I say this mainly because the yields are very high for this reaction and also any unreacted phenylalanine will stay in the strongly acidic aqueous
phase (if you follow the workup highlighted at the end of the article).
The nitrile of tyrosine would be 4-hydroxyphenylacetonitrile
" arginin " 1-(3-cyanopropyl)guanidine although I do not expect that to be attainable via the method we are talking
about (I think the guanidine group will react as well with the hypochlorous acid)
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dr. nick
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thanks!
and: damned, this thread doesn't help much to get fentanyls out of my mind - especially when thinking of decarboxylation, a mannich as mentioned
elsewhere with another amine instead of aniline and reaction of the product with acetic anhydrid or even acetic acid instead of propionic anhydride
(as also mentioned elsewhere) - with a decent testing method this would be fun for years, even for kitchen chemists ... *arrrr, get off my mind, evil
amino acid possibilities, you're so off topic* ...
of course you can well i couldn\'t before
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