The Vespiary

The Hive => Newbee Forum => Topic started by: Purepacker on February 19, 2004, 03:09:00 PM

Title: Homoserine to GHB ?
Post by: Purepacker on February 19, 2004, 03:09:00 PM

SWIM has 50 grams of homoserine. Since the homoserine structure is almost identical to GHB (except for the 2-amino functional group) the question rose whether one can remove the amino group without too much problems ? Any input would be appreciated....

Title: Homoresine biosynthesis
Post by: silenziox on February 19, 2004, 04:37:00 PM

Homoserine biosynthesis references found from google:

http://biocyc.org%3A1555/ECOLI/new-image?type=PATHWAY&object=HOMOSERSYN-PWY (http://biocyc.org%3A1555/ECOLI/new-image?type=PATHWAY&object=HOMOSERSYN-PWY)

Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)

L-homoserine / 2-amino-4-hydroxybutanoic acid ("C(=O)(C(CCO)N)O")



Anyways, you'd have to de-aminate somehow to get 5-hydroxypentanoic acid (GVL / gamma-valerolactone) and then de-methylate it to get 4-hydroxybutyric acid (GBL / gamma-butyrolactone).... Impossible.

Same would go for 4-Aminobutylate and D-aspartate (for 1,4-BDO you'd have to de-hydeogenate it)...

Check out also

Post 466474 (https://www.thevespiary.org/talk/index.php?topic=11040.msg46647400#msg46647400)

(adroit_synth: "2-aminomethyl-THF/Tetrahydrofurfurylamine ->THF", Newbee Forum)

Title: Count your carbons
Post by: Rhodium on February 19, 2004, 06:16:00 PM

Count your carbons - how did you go from 2-amino-4-hydroxy-butanoic acid to 4-hydroxy-pentanoic acid just like that?

Title: Shit. My mistake.
Post by: silenziox on February 19, 2004, 06:28:00 PM

I'm drunk  ;D  and was thinking the time I had some valerolactone which I furiously tried to de-methylate.
I meant to say 4-hydroxy-2-methylbutanoic acid.

Sorry for the confusion.

Title: I must have been...
Post by: Purepacker on February 23, 2004, 02:22:00 PM

drunk too...  :P