- (S )-2- amino-4- hydroxybutyric acid
- (S )-2- amino-4- hydroxybutanoic acid
- 672-15-1 (L -homoserine )
- 6027-21-0 (D -homoserine )
- 1927-25-9 (DL -homoserine )
Decomposition: 203 ° C
Slightly soluble in water
Template: Infobox chemical / molecular formula search available
L -homoserine [ Synonyms: ( S)- homoserine ] is a non-protein, polar α -amino acid. It is an intermediate in the biochemical degradation of L- methionine.
This results in the metabolism with L -cysteine from L- homocysteine with L-serine to Thiolübertragung under catalysis of the Cystathionine - synthase ( 1) and cystathionase (2).
Here, cystathionine formed as a temporary intermediate product from the condensation of L- serine with L- homocysteine elimination of water at the thiol or hydroxy end. With subsequent hydrolysis caused by splitting ( 2) re- L-cysteine and L-homoserine.
- Failure ( 1 ) ⇒ homocysteinuria
- Failure ( 2 ) ⇒ Cystathionurie
L-homoserine can release ammonia under the influence of homoserine deaminase and converted to α - ketobutyrate. This can, for α - aminobutyrate are transaminates unite with CoA -SH to propionyl -CoA or under recovery of NADH / H and decarboxylation.
L -homoserine is produced on a large scale by fermentation in Slovakia at the Evonik subsidiary Fermas in Slovenská Ľupča. The unnatural amino acid is thus produced from renewable resources.
( S)- homoserine is a starting material for the manufacture of many interesting organic chemical intermediates, these include the following heterocycles: (S )-3- aminopyrrolidin, (S )-3- amino butyrolactone, (S )-3- Aminotetrahydrothiophen, (S )-3- Aminotetrahydrofuran and (S) - azetidine carboxylic acid.