Homoserine to GHB ?

[Purepacker]

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....

[silenziox]

Homoserine biosynthesis references found from google:

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

Molecule:

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

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

[Rhodium]

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

[silenziox]

I'm drunk    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.

[Purepacker]

drunk too...