Homoserine

• (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 )

Colorless solid

Fixed

Decomposition: 203 ° C

Slightly soluble in water

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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.

Production

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.

Use

( 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.