Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
 Pages:  1  2
Author: Subject: Playing with tyrosine
tr41414
Hazard to Self
**




Posts: 56
Registered: 14-9-2006
Location: EU
Member Is Offline

Mood: No Mood

[*] posted on 4-7-2007 at 12:26


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 :D)...
View user's profile Visit user's homepage View All Posts By User
smuv
International Hazard
*****




Posts: 842
Registered: 2-5-2007
Member Is Offline

Mood: Jingoistic

[*] posted on 4-7-2007 at 13:54


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
View user's profile View All Posts By User
dr. nick
Hazard to Self
**




Posts: 94
Registered: 20-6-2004
Location: Doh!land
Member Is Offline

Mood: yes

[*] posted on 5-7-2007 at 13:08


@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
View user's profile View All Posts By User
smuv
International Hazard
*****




Posts: 842
Registered: 2-5-2007
Member Is Offline

Mood: Jingoistic

[*] posted on 10-7-2007 at 22:59


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)
View user's profile View All Posts By User
dr. nick
Hazard to Self
**




Posts: 94
Registered: 20-6-2004
Location: Doh!land
Member Is Offline

Mood: yes

[*] posted on 11-7-2007 at 11:56


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
View user's profile View All Posts By User
 Pages:  1  2

  Go To Top